(3B,22E)-胆甾-5,22-二烯-3-醇 | 34347-28-9

• 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
• 中文名称: (3B,22E)-胆甾-5,22-二烯-3-醇
• 英文名称: 22-dehydrocholesterol
• 英文别名: (22E)-24-norcholesta-5,22-dien-3β-ol；5,22-cholesta-5-trans-22-dien-3β-ol；Cholesta-5α,22(E)-dien-3β-ol；22-trans-cholesta-5,22-diene-3β-ol；22-trans-5,22-cholesta-dien-3β-ol；22-trans-cholesta-5,22-dien-3β-ol；(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-6-methylhept-3-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
• CAS: 34347-28-9
• 化学式: C₂₇H₄₄O
• 分子量: 384.646
• InChiKey: UPGTYLFCVNHBTN-OFAYOZIESA-N

物化性质

• 沸点：
  479.9±14.0 °C(Predicted)
• 密度：
  0.99±0.1 g/cm3(Predicted)
• 熔点：
  133.5-134.0 °C
• 保留指数：
  3070;3084.7

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3B,22E)-胆甾-5,22-二烯-3-醇 生成 [(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-6-methylhept-3-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] 4-methylbenzenesulfonate
  参考文献：
  名称：

  TAKATSUTO, SUGURU;IKEKAWA, NOBUO, CHEM. AND PHARM. BULL., 35,(1987) N 7, 3006-3010

  摘要：

  DOI：
• 作为产物：
  描述：

  溴化异戊基三苯基磷 生成 (3B,22E)-胆甾-5,22-二烯-3-醇
  参考文献：
  名称：

  Synthesis of sterols with modified side chains

  摘要：

  DOI：

  10.1016/0039-128x(75)90010-0

文献信息

• Saturated and unsaturated sterols of nitrogen-fixing blue-green algae (cyanobacteria)
  作者：Manfred Kohlhase、Peter Pohl

  DOI：10.1016/0031-9422(88)80434-5

  日期：1988.1

  Abstract Five species of filamentous nitrogen-fixing blue-green algae (Cyanobacteria), ( Anabaena cylindrica , Anabaena solitaria , Anabaena viguieri ,

  摘要 丝状固氮蓝绿藻（Cyanobacteria）5种，（圆柱鱼腥藻、孤鱼鱼腥藻、鱼腥藻、
• Synthesis of 28-norbrassinolide.
  作者：SUGURU TAKATSUTO、BAIPING YING、MASUO MORISAKI、NOBUO IKEKAWA

  DOI：10.1248/cpb.29.903

  日期：——

  28-Norbrassinolide (2α, 3α, 22R, 23R-tetrahydroxy-B-homo-7-oxa-5α-cholestan-6-one), which is an analog of the plant growth promoting steroidal lactone, brassinolide, was synthesized via 22R, 23R-dihydroxycholesterol. Syntheses of the other C-22, 23 stereoisomers of 22, 23-dihydroxycholesterol were also described.

  28-Norbrassinolide (2α, 3α, 22R, 23R-tetrahydroxy-B-homo-7-oxa-5α-cholestan-6-one) 是植物生长促进类固醇内酯 brassinolide 的类似物，由 22R，23R-二羟基胆固醇合成。此外，还介绍了 22，23-二羟基胆固醇的其他 C-22，23 立体异构体的合成。
• Preparation of some unsaturated side chain derivatives of cholesterol
  作者：Henry W. Kircher、Fumiko U. Rosenstein

  DOI：10.1021/jo00348a023

  日期：1982.4
• Metathesis reactions of Δ22-steroids
  作者：Dorota Czajkowska、Jacek W. Morzycki

  DOI：10.1016/j.tetlet.2009.03.191

  日期：2009.6

  Metathesis reactions of Delta(22)-steroids are studied. The cross metathesis reactions of model Delta(22)-steroids with excess of simple alkenes are sluggish or do not occur at all. In contrast, derivatives of both trans- and cis-Delta(22)-cholesterol undergo ring closing metathesis reactions but the former reacts faster. However, the side chain double bond in stigmasterol and ergosterol is too crowded for metathesis reactions promoted by currently available catalysts. (C) 2009 Elsevier Ltd. All rights reserved.
• The synthesis and the mass and nuclear magnetic resonance spectra of side chain isomers of cholesta-5,22-dien-3β-ol and cholesta-5,22,24-trien-3β-ol
  作者：Roderick F.N. Hutchins、Malcolm J. Thompson、James A. Svoboda

  DOI：10.1016/s0039-128x(70)80008-3

  日期：1970.1