13(R)-hydroxystemodan-2-one | 783341-92-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 13(R)-hydroxystemodan-2-one
• 英文别名: (1R,2S,7S,10S,12S,13R)-13-hydroxy-2,6,6,13-tetramethyltetracyclo[10.3.1.01,10.02,7]hexadecan-4-one
• CAS: 783341-92-4
• 化学式: C₂₀H₃₂O₂
• 分子量: 304.473
• InChiKey: MTHCEQRYJNYWKN-DZJPNTAKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 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：

  13(R)-hydroxystemodan-2-one 在 sodium tetrahydroborate 、 Rhyzopus oryzae ATCC 11145 作用下， 以 甲醇 为溶剂， 反应 192.3h， 生成 2β,7β,13(R)-trihydroxystemodane
  参考文献：
  名称：

  Investigation of the importance of the C-2 and C-13 oxygen functions in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145

  摘要：

  Incubation of 2alpha,13(R)-dihydroxystemodane (3) with Rhizopus oryzae ATCC 11145 gave 2alpha,7beta,13(R)-trihydroxystemodane (11) while biotransformation of 13(R)-hydroxystemodan-2-one (5) yielded 6alpha,13(R)-dihydroxystemodan-2-one (12) and 7beta,13(R)-dihydroxystemodan-2-one (13). Bioconversion of 2beta,13(R)-dihydroxystemodane (7) with Rhizopus afforded 2beta,7,13(R)-trihydroxystemodane (14). The results complement data from our previous work and provide more information about the effect of functional groups of stemodane substrates on the site of hydroxylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2004.05.016
• 作为产物：
  描述：

  2α,13(R)-dihydroxystemodane 在 jones reagent 作用下， 以 丙酮 为溶剂， 反应 0.5h， 以488 mg的产率得到13(R)-hydroxystemodan-2-one
  参考文献：
  名称：

  Investigation of the importance of the C-2 and C-13 oxygen functions in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145

  摘要：

  Incubation of 2alpha,13(R)-dihydroxystemodane (3) with Rhizopus oryzae ATCC 11145 gave 2alpha,7beta,13(R)-trihydroxystemodane (11) while biotransformation of 13(R)-hydroxystemodan-2-one (5) yielded 6alpha,13(R)-dihydroxystemodan-2-one (12) and 7beta,13(R)-dihydroxystemodan-2-one (13). Bioconversion of 2beta,13(R)-dihydroxystemodane (7) with Rhizopus afforded 2beta,7,13(R)-trihydroxystemodane (14). The results complement data from our previous work and provide more information about the effect of functional groups of stemodane substrates on the site of hydroxylation. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2004.05.016

文献信息

• Stemodane skeletal rearrangement: chemistry and microbial transformation
  作者：Glenroy D.A. Martin、William F. Reynolds、Paul B. Reese

  DOI：10.1016/j.phytochem.2005.02.019

  日期：2005.4

  Solvolytic rearrangement of the C/D ring system of the tetracyclic diterpenoid stemodinone (2) afforded the compounds 15(13-->12)abeo-13beta-hydroxystemaran-2-one (5) and 15(8-->9)abeo-8beta(H)-12beta-hydroxystachan-2-one (10). Terpene 5 possesses a novel diterpene skeleton. Oxidation of these compounds yielded their respective diketones. Bioconversion of 5 by Rhizopus oryzae yielded 15(13-->12)abeo-7beta

  四环二萜类固醇甾酮 (2) 的 C/D 环系统的溶剂分解重排得到化合物 15(13-->12)abeo-13beta-hydroxystemaran-2-one (5) 和 15(8-->9)abeo -8beta(H)-12beta-hydroxystachan-2-one (10)。萜烯 5 具有新的二萜骨架。这些化合物的氧化产生它们各自的二酮。米根霉对 5 的生物转化产生 15(13-->12)abeo-7beta,13beta-dihydroxystemaran-2-one (18)，而 10 的微生物转化提供 15(8-->9)abeo-8beta(H)- 6alpha,12beta-dihydroxystachan-2-one (19), 15(8-->9)abeo-8beta(H)-7beta,12beta-dihydroxystachan-2-one (20) 和 15(8-->9)abeo