(22E,24R)-stigmasta-1,4-dien-3-one | 64700-25-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: (22E,24R)-stigmasta-1,4-dien-3-one
• 英文别名: stigmasta-1,4-dien-3-one；stigmast-1,4-dien-3-one；(8S,9S,10R,13R,14S,17R)-17-[(2R,5R)-5-ethyl-6-methylheptan-2-yl]-10,13-dimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
• CAS: 64700-25-0
• 化学式: C₂₉H₄₆O
• 分子量: 410.684
• InChiKey: JGPRZIQBLSTSOH-XJZKHKOHSA-N

物化性质

• 熔点：
  89-91 °C(Solv: methanol (67-56-1))
• 沸点：
  504.5±20.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.5
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (22E,24R)-stigmasta-1,4-dien-3-one 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以75.5%的产率得到stigmasta-1,5-dien-3-one
  参考文献：
  名称：

  使用豆甾醇合成 1α-羟基维生素 D5 和相关化合物的功能性中间体的实用简便途径

  摘要：

  As a functional and versatile intermediate for the synthesis of la-hydroxyvitamin D-5 and related compounds, 1 alpha,2 alpha-epoxy-3 beta-hydroxystigmasta-5,7-diene was synthesized by a practical and facile 17-step route from stigmasterol in 17% overall yield.

  DOI：

  10.3987/com-15-s(t)6
• 作为产物：
  描述：

  豆甾醇 在 N-甲基-4-哌啶酮 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 、 甲苯 为溶剂， 反应 26.0h， 生成 (22E,24R)-stigmasta-1,4-dien-3-one
  参考文献：
  名称：

  使用豆甾醇合成 1α-羟基维生素 D5 和相关化合物的功能性中间体的实用简便途径

  摘要：

  As a functional and versatile intermediate for the synthesis of la-hydroxyvitamin D-5 and related compounds, 1 alpha,2 alpha-epoxy-3 beta-hydroxystigmasta-5,7-diene was synthesized by a practical and facile 17-step route from stigmasterol in 17% overall yield.

  DOI：

  10.3987/com-15-s(t)6

文献信息

• APPLICATION A TITRE DE MEDICAMENTS DE DERIVES DE CHOLEST-4-EN-3- ONE, COMPOSITIONS PHARMACEUTIQUES LES RENFERMANT ET NOUVEAUX DERIVES
  申请人：Trophos

  公开号：EP1601363B1

  公开（公告）日：2012-06-20
• Biocatalytic Steroidal 9α‐Hydroxylation and Fragmentation Enable the Concise Chemoenzymatic Synthesis of 9,10‐Secosteroids
  作者：Hanxin Song、Zeliang Zhang、Chunyang Cao、Zhijun Tang、Jinghan Gui、Wen Liu

  DOI：10.1002/anie.202319624

  日期：2024.4.15

  9,10‐Secosteroids are an important group of marine steroids with diverse biological activities. Herein, we report a chemoenzymatic strategy for the concise, modular, and scalable synthesis of ten naturally occurring 9,10‐secosteroids from readily available steroids in three to eight steps. The key feature lies in utilizing a Rieske oxygenase‐like 3‐ketosteroid 9α‐hydroxylase (KSH) as the biocatalyst to achieve efficient C9−C10 bond cleavage and A‐ring aromatization of tetracyclic steroids through 9α‐hydroxylation and fragmentation. With synthesized 9,10‐secosteroides, structure–activity relationship was evaluated based on bioassays in terms of previously unexplored anti‐infective activity. This study provides experimental evidence to support the hypothesis that the biosynthetic pathway through which 9,10‐secosteroids are formed in nature shares a similar 9α‐hydroxylation and fragmentation cascade. In addition to the development of a biomimetic approach for 9,10‐secosteroid synthesis, this study highlights the great potential of chemoenzymatic strategies in chemical synthesis.