(22-trans)-3β-hydroxy-cholest-5,22-diene-24-one | 89495-47-6

• 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: (22-trans)-3β-hydroxy-cholest-5,22-diene-24-one
• 英文别名: (22-trans)-hydroxy-3β-cholestadiene-5,22-one-24；(20S)-3β-hydroxycholesta-5,22(E)-dien-24-one；(22E)-3β-hydroxycholesta-5,22-dien-24-one；(22E)-3β-hydroxycholest-5,22-dien-24-one；(22E)-3β-hydroxycholesta-5,22-dien-24-on；cholest-5,22-dien-3β-ol-24-one；(22e)-3beta-Hydroxycholesta-5,22-dien-24-one；(E,6R)-6-[(3S,8S,9S,10R,13R,14S,17R)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-methylhept-4-en-3-one
• CAS: 89495-47-6
• 化学式: C₂₇H₄₂O₂
• 分子量: 398.629
• InChiKey: VMXMLOFNEQBYHM-INVHITAPSA-N

物化性质

• 沸点：
  518.1±23.0 °C(Predicted)
• 密度：
  1.04±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (22-trans)-3β-hydroxy-cholest-5,22-diene-24-one 在 platinum(IV) oxide 氢气 、 sodium hydride 、 二甲基亚砜 作用下， 以 乙酸乙酯 为溶剂， 反应 4.5h， 生成 5,24(28)-胆甾二烯-24-亚甲基-3beta-醇
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3β,6α-diol

  摘要：

  Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K2CO3 in a solid-liquid phase-transfer Wittig reaction. Construction of the steroidal nucleus was finished by oxidation of 24-methylenecholest-5-en-3beta-ol (9) with pyridinium chlorochromate (PCC) in dichloromethane at ambient temperature and by reduction of 24-methylenecholest-4-en-3,6-dione (10) with NaBH4 in the presence of CeCl3.7H(2)O. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00059-4
• 作为产物：
  描述：

  豆甾醇 在 盐酸 、 iodobenzene dibromide 、 potassium carbonate 、 臭氧 、 formamide 作用下， 以 乙腈 为溶剂， 反应 33.0h， 生成 (22-trans)-3β-hydroxy-cholest-5,22-diene-24-one
  参考文献：
  名称：

  Synthesis of polyhydroxysterols (III): synthesis and structural elucidation of 24-methylenecholest-4-en-3β,6α-diol

  摘要：

  Using stigmasterol as the starting material, 24-methylenecholest-4-en-3beta,6alpha-diol (2) was synthesized in eight steps in 13% overall yield. The introduction of the sterol side-chain was carried out using (3-methyl-2-oxobutyl)-triphenylarsonium bromide (11) and K2CO3 in a solid-liquid phase-transfer Wittig reaction. Construction of the steroidal nucleus was finished by oxidation of 24-methylenecholest-5-en-3beta-ol (9) with pyridinium chlorochromate (PCC) in dichloromethane at ambient temperature and by reduction of 24-methylenecholest-4-en-3,6-dione (10) with NaBH4 in the presence of CeCl3.7H(2)O. (C) 2002 Elsevier Science Inc. All rights reserved.

  DOI：

  10.1016/s0039-128x(02)00059-4

文献信息

• Coordination of Sodium Cation to an Oxygen Function and Olefinic Double Bond to Form Molecular Adduct Ion in Fast Atom Bombardment Mass Spectrometry.
  作者：Naoko Morisaki、Hisayoshi Kobayashi、Yumiko Yamamura、Masuo Morisaki、Kazuo Nagasawa、Yuichi Hashimoto

  DOI：10.1248/cpb.50.935

  日期：——

  Steroidal allylic alcohols formed Na+ adduct ion peaks [M+Na]+ by the addition of NaCl in FAB mass spectrometry. A comparison of the intensities of the adduct ion peaks of allylic alcohols with those of the corresponding saturated alcohols and olefin suggested that the olefinic double bond and the proximal hydroxyl group had coordinated to Na+. The adduct ion was stable and did not undergo dehydroxylation

  在FAB质谱法中，通过添加NaCl，甾体烯丙醇形成Na +加成离子峰[M + Na] +。烯丙基醇与相应的饱和醇和烯烃的加合离子峰强度的比较表明，烯烃双键和近端羟基已与Na +配位。加合物离子是稳定的并且没有经历脱羟基。我们认为，Na +加合物可用于在FAB质谱条件下易于脱羟基的烯丙醇的分子量测定。还研究了α，β-不饱和羰基化合物的Na +加成离子。
• Studies on the Biosynthesis of Antheridiol
  作者：C. R. Popplestone、A. M. Unrau

  DOI：10.1139/v74-074

  日期：1974.2.1

  reproduction in the aquatic fungus Achlya bisexualis is governed by antheridiol, a C29 sterol, secreted by the female plant and which initiates formation of antheridial hyphae on the male plant. Tracer studies showed that naturally occurring fucosterol supplied the necessary carbon skeleton for antheridiol. Labelling and trapping studies with a series of hypothetic sterol precursors have indicated the

  水生真菌 Aclya bisexualis 的有性繁殖由雌二醇（一种 C29 甾醇）控制，由雌性植物分泌，并在雄性植物上开始形成雄性菌丝。示踪剂研究表明，天然岩藻甾醇为花胶醇提供了必要的碳骨架。用一系列假设的甾醇前体进行的标记和捕获研究表明了参与制作 antheridiol 侧链的生物学序列。
• Koch, Patrick; Nakatani, Yoichi; Luu, Bang, Bulletin de la Societe Chimique de France, 1983, vol. 2, # 7/8, p. 185 - 194
  作者：Koch, Patrick、Nakatani, Yoichi、Luu, Bang、Ourisson, Guy

  DOI：——

  日期：——
• Khripach, V. A.; Zavadskaya, M. I.; Kotyatkina, A. I., Russian Journal of Organic Chemistry, 1993, vol. 29, # 7.1, p. 1134 - 1136
  作者：Khripach, V. A.、Zavadskaya, M. I.、Kotyatkina, A. I.、Drachenova, O. A.

  DOI：——

  日期：——
• ——
  作者：R. P. Litvinovskaya、N. V. Koval'、V. A. Khripach

  DOI：10.1023/a:1016373807105

  日期：——

  Steroidal 1,4,6-trien-3-ones which are precursors of 1alpha-hydroxylated vitamin D and its analogs were synthesized starting from 3beta-hydroxy-Delta(5)-20-dihydroisoxazolyl steroids and their open-chain derivatives.