11-Deoxy-PGF(1α)-methylester | 51794-46-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 11-Deoxy-PGF(1α)-methylester
• 英文别名: methyl 7-[(1R,2S,5R)-2-hydroxy-5-[(E,3S)-3-hydroxyoct-1-enyl]cyclopentyl]heptanoate
• CAS: 51794-46-8
• 化学式: C₂₁H₃₈O₄
• 分子量: 354.53
• InChiKey: PFVCBTJOTZXQSG-ZNBICKNKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  25
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  11-Deoxy-PGF(1α)-methylester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 17.0h， 以90%的产率得到7-[(1R,2S,5R)-2-羟基-5-[(E,3S)-3-羟基辛-1-烯基]环戊基]庚酸
  参考文献：
  名称：

  A Catalytic Asymmetric Synthesis of 11-Deoxy-PGF_1α Using ALB, a Heterobimetallic Multifunctional Asymmetric Complex

  摘要：

  A catalytic asymmetric synthesis of 11-deoxy-PGF(1 alpha) has been achieved using a cascade Michael-aldol reaction as a key step. This cascade reaction was efficiently promoted by a catalytic use of AlLibis[(S)-binaphthoxide] complex (ALB) to give the three-component coupling product at room temperature in 92% ee and in 84% yield. The three-component coupling product was then converted to (+)-11-deoxy-PGF(1 alpha) through several steps, including an oxidative decarboxylation, an aldol reaction, and a Wharton reaction. Moreover, the racemic enone, 20 was transformed into 21, the three-component coupling product, a potential intermediate for PGF(1 alpha), in 97% ee and in 75% yield through catalytic kinetic resolution.

  DOI：

  10.1021/jo9723319
• 作为产物：
  描述：

  9,15-Dioxo-prosten-(13-trans)-saeure-methylester 生成 11-Deoxy-PGF(1α)-methylester
  参考文献：
  名称：

  MIFTAXOV, M. S.;AKBUTINA, F. A.;VALEEV, F. A.;KUCHIN, A. V.;BERG, A. A.;O+, ZH. ORGAN. XIMII, 23,(1987) N 12, 2553-2559

  摘要：

  DOI：

文献信息

• TOLSTIKOV, G. A.;AKBUTINA, F. A.;ADLER, M. EH.;SIDOROV, N. N.;KUCHIN, A. +, ZH. ORGAN. XIMII, 24,(1988) N 12, S. 2622-2624
  作者：TOLSTIKOV, G. A.、AKBUTINA, F. A.、ADLER, M. EH.、SIDOROV, N. N.、KUCHIN, A. +

  DOI：——

  日期：——
• Tolstikov, G. A.; Akbutina, F. A.; Adler, M. E., Russian Journal of Organic Chemistry, 1988, vol. 24, # 12, p. 2369 - 2370
  作者：Tolstikov, G. A.、Akbutina, F. A.、Adler, M. E.、Sidorov, N. N.、Kuchin, A. V.、Miftakhov, M. S.

  DOI：——

  日期：——