호스필린

Horsfiline
호스필린
Horsfiline.svg
이름
우선 IUPAC 이름
(3R)-5-메톡시-1γ-메틸스피로[인돌-3,3γ-피롤리딘]-2(1H)-원
식별자
3D 모델(JSmol)
켐스파이더
  • InChI=1S/C13H16N2O2/c1-15-6-13(8-15)10-7-9(17-2)3-4-11(10)14-12(13)16/h3-4,7H,5-6,8H2,1-2H3,14H(14H)
    키: RVOLLKGLGLG-ZDUSSCGKSA-N checkY
  • InChI=1/C13H16N2O2/c1-15-6-13(8-15)10-7-9(17-2)3-4-11(10)14-12(13)16/h3-4,7H,5-6,8H2,1-2H3(13,14)T
    키: RVOLLKGLGLG-ZDUSSCGKBT
  • O=C2Nc1c(cc(OC)cc1)[C@] 23CN(C)CC3
특성.
C13H16N2O2
몰 질량 232.283 g/120−1
녹는점 125~126°C(257~259°F, 398~399K)
달리 명시되지 않은 한 표준 상태(25°C[77°F], 100kPa)의 재료에 대한 데이터가 제공됩니다.

호스필린은 전통적인 한약재에 사용되는 [1]호스필디아 슈퍼바 식물에서 발견되는 옥신돌 알칼로이드입니다.그것은[2][3][4][5][6][7][8] 진통[medical citation needed] 효과를 가지고 있고 편리한 경로를 통해 그것을 합성하고 진통 효과를 [9][10]개선할 수 있는 유사체와 유도체를 개발하기 위해 연구 대상이 되어 왔다.

스피로인돌론 클래스의 멤버입니다.엘라코민은 비슷한 화학 구조를 가지고 있다.

레퍼런스

  1. ^ Jossang A, Jossang P, Hadi HA, Sevenet T, Bodo B (1991). "An oxindole alkaloid from Horsfieldia superba". Journal of Organic Chemistry. 56 (23): 6527–6530. doi:10.1021/jo00023a016.
  2. ^ Lakshmaiah G, Kawabata T, Shang M, Fuji K (March 1999). "Total Synthesis of (-)-Horsfiline via Asymmetric Nitroolefination". The Journal of Organic Chemistry. 64 (5): 1699–1704. doi:10.1021/jo981577q. PMID 11674239.
  3. ^ Cravotto G, Giovenzana GB, Pilati T, Sisti M, Palmisano G (December 2001). "Azomethine ylide cycloaddition/reductive heterocyclization approach to oxindole alkaloids: asymmetric synthesis of (-)-horsfiline". The Journal of Organic Chemistry. 66 (25): 8447–53. doi:10.1021/jo015854w. PMID 11735524.
  4. ^ Murphy JA, Tripoli R, Khan TA, Mali UW (July 2005). "Novel phosphorus radical-based routes to horsfiline". Organic Letters. 7 (15): 3287–9. doi:10.1021/ol051095i. PMID 16018642.
  5. ^ Trost BM, Brennan MK (May 2006). "Palladium asymmetric allylic alkylation of prochiral nucleophiles: horsfiline". Organic Letters. 8 (10): 2027–30. doi:10.1021/ol060298j. PMC 2565574. PMID 16671773.
  6. ^ Hong S, Jung M, Park Y, Ha MW, Park C, Lee M, Park HG (July 2013). "Efficient enantioselective total synthesis of (-)-horsfiline". Chemistry: A European Journal. 19 (29): 9599–605. doi:10.1002/chem.201301008. PMID 23836402.
  7. ^ Mukaiyama T, Ogata K, Sato I, Hayashi Y (October 2014). "Asymmetric organocatalyzed Michael addition of nitromethane to a 2-oxoindoline-3-ylidene acetaldehyde and the three one-pot sequential synthesis of (-)-horsfiline and (-)-coerulescine". Chemistry: A European Journal. 20 (42): 13583–8. doi:10.1002/chem.201403932. PMID 25155110.
  8. ^ Buev EM, Moshkin VS, Sosnovskikh VY (December 2017). "Nonstabilized Azomethine Ylides in the Mannich Reaction: Synthesis of 3,3-Disubstituted Pyrrolidines, Including Oxindole Alkaloids". The Journal of Organic Chemistry. 82 (23): 12827–12833. doi:10.1021/acs.joc.7b02193. PMID 29048900.
  9. ^ Tsai YC, Liou JP, Liao R, Cheng CY, Tao PL (July 1998). "C-alkylated spiro[benzofuran-3(2H),4'-1'-methyl-piperidine-7-ols] as potent opioids: a conformation-activity study". Bioorganic & Medicinal Chemistry Letters. 8 (14): 1813–8. doi:10.1016/S0960-894X(98)00318-7. PMID 9873439.
  10. ^ Alf Claesson, Britt-Marie Swahn, Odd-Geir Berge.진통제 역할을 하는 스피록신돌 유도체.미국 특허 6774132