tomentogenin | 3513-00-6

• 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: tomentogenin
• 英文别名: (3S,5S,8R,9S,10S,12R,13S,14S,17S)-17-[(1S)-1-hydroxyethyl]-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,15,16-dodecahydro-1H-cyclopenta[a]phenanthrene-3,12,14,17-tetrol
• CAS: 3513-00-6
• 化学式: C₂₁H₃₆O₅
• 分子量: 368.514
• InChiKey: VLJHJGYZWGQIKC-AVOYBPDBSA-N

物化性质

• 熔点：
  265-268 °C
• 沸点：
  542.1±50.0 °C(Predicted)
• 密度：
  1.277±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  26
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  101
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  utendin 在 platinum(IV) oxide 氢气 作用下， 以 溶剂黄146 、 乙酸乙酯 为溶剂， 生成 tomentogenin
  参考文献：
  名称：

  Studies on the constituents of asclepiadaceae plants. 40. Absolute configurations of tomentogenin and utendin.

  摘要：

  通过 20-O-邻硝基苯甲酰基衍生物的圆二色性实验，确定了托莫特苷元和乌藤素的 C-20 构型为 s。根据这些结果，确定了托莫特苷元和乌藤素的绝对构型分别为 5α-孕-3β、12β、14β、17β、20α-戊醇和孕-5-烯-3β、12β、14β、17β、20α-戊醇。

  DOI：

  10.1248/cpb.24.2457

文献信息

• Studies on the constituents of asclepiadaceae plants. XXXVI. Component of Marsdenia tomentosa Decne: Structure of tomentonin, tomentodin and dehydrotomentosin and difference in the reactivity between utendin and tomentogenin diesters on mild alkaline hydrolysis.
  作者：HIDEO SETO、KOJI HAYASHI、HIROSHI MITSUHASHI

  DOI：10.1248/cpb.24.443

  日期：——

  Three new polyoxypregnane derivatives, tomentonin (12β-O-dihydrotigloyl-20-O-acetyltomentogenin), tomentodin (12β-O-cinnamoyl-20-O-acetyltomentogenin), and dehydrotomentosin (12β-O-tigloyl-20-O-acetylutendin), were isolated from the stem of Marsdenia tomentosa DECNE. Dehydrotomentosin underwent an internal acyl migration from C-12β-OH to C-20-OH on mild alkaline hydrolysis to afford a monoester, but tomentonin and tomentodin did not. The remarkable difference in the reactivity between toementogenin and utendin diesters on this condition was discussed. Tomentonin is the first example of a tomentogenin derivative with an ester linking of dihydrotiglic acid or 2-methylbutyric acid isolated from Asclepiadaceae plants.

  从茜草茎（Marsdenia tomentosa DECNE）中分离出了三种新的聚氧孕烷烃衍生物：托莫托宁（12β-O-二氢-20-O-乙酰基托莫托宁）、托莫托丁（12β-O-肉桂酰-20-O-乙酰基托莫托宁）和脱氢托莫托宁（12β-O-三酰基-20-O-乙酰基utendin）。在温和的碱性水解过程中，脱氢托梦多糖苷会发生从 C-12β-OH 到 C-20-OH 的内部酰基迁移，生成单酯，但托梦多糖苷和托梦多糖苷不会发生这种迁移。讨论了在这种条件下，交门冬皂甙和乌藤素二酯之间反应性的显著差异。托门托宁是从被子植物中分离出来的第一个具有二氢二甘酸或 2-甲基丁酸酯连接的托门托宁衍生物的实例。
• Constituents of asclepiadaceae plants. XXXV. Component of Marsdenia tomentosa decne. Structure of tomentin and dehydrotomentin.
  作者：HIDEO SETO、KOJI HAYASHI、HIROSHI MITSUHASHI

  DOI：10.1248/cpb.23.2397

  日期：——

  Two new polyoxypregnane derivatives, tomentin (12β-O-, 20-O-diacetyltomentogenin) and dehydrotomentin (12β-O, 20-O-diacetylutendin), were isolated from the stem of Marsdenia tomentosa. Dehydrotomentin is a diester possessing the utendin skeleton to be isolated from the Asclepiadaceae plants for the first time. Very characteristic fragment pattern for tomentogenin derivatives was observed in the mass spectrum of tomentin.

  从毛叶马兜铃的茎中分离出两种新的聚氧孕烷衍生物：毛叶马兜铃素（12β-O-, 20-O-二乙酰基毛叶马兜铃素）和脱氢毛叶马兜铃素（12β-O, 20-O-二乙酰基毛叶马兜铃素）。脱氢毛叶马兜铃素是一种二酯，具有毛叶马兜铃素骨架，首次从马兜铃科植物中分离出来。在毛叶马兜铃素的质谱中观察到了毛叶马兜铃素衍生物非常典型的片段模式。
• Constituents of asclepiadaceae plants. XXXIII. Component of Marsdenia tomentosa Decne. Structure of tomentosin.
  作者：HIDEO SETO、KOJI HAYASHI、HIROSHI MITSUHASHI

  DOI：10.1248/cpb.23.1552

  日期：——

  A new polyoxypregnane derivative, tomentosin (12β-O-tigloyl-20-O-acetyl-tomentogenin) was isolated from the stem of Marsdenia tomentosa. Tomentosin is the first example of the diester possessing a tomentogenin skeleton to be isolated from the Asclepiadaceae plant, and it did not undergo any internal acyl migration which occurrs on mild alkaline hydrolysis of C-12β, 20-diester of sarcostin and other polyoxypregnane derivatives.

  一种新的聚氧孕烷衍生物——毛地黄皂苷（12β-O-tigloyl-20-O-acetyl-tomentogenin）从毛地黄茎中分离出来。毛地黄皂苷是从马兜铃科植物中分离出的第一个具有毛地黄皂苷骨架的二酯，它没有发生任何内部酰基迁移，而酰基迁移发生在C-12β、20-二酯的缬草皂苷和其他聚氧孕烷衍生物的温和碱性水解中。
• Scalable C–H Oxidation with Copper: Synthesis of Polyoxypregnanes
  作者：Yi Yang See、Aaron T. Herrmann、Yoshinori Aihara、Phil S. Baran

  DOI：10.1021/jacs.5b09463

  日期：2015.11.4

  Steroids bearing C12 oxidations are widespread in nature, yet only one preparative chemical method addresses this challenge in a low-yielding and not fully understood fashion: Schonecker's Cu-mediated oxidation. This work shines new light onto this powerful C-H oxidation method through mechanistic investigation, optimization, and wider application. Culminating in a scalable, rapid, high-yielding, and operationally simple protocol, this procedure is applied to the first synthesis of several parent polyoxypregnane natural products, representing a gateway to over 100 family members.
• Seto,H. et al., Chemical and pharmaceutical bulletin, 1976, vol. 24, p. 1552 - 1554
  作者：Seto,H. et al.

  DOI：——

  日期：——