stemod-12-ene | 41703-78-0

• 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: stemod-12-ene
• 英文别名: (1R,2S,7S,10S,12S)-2,6,6,13-tetramethyltetracyclo[10.3.1.01,10.02,7]hexadec-13-ene
• CAS: 41703-78-0
• 化学式: C₂₀H₃₂
• 分子量: 272.474
• InChiKey: OQLQRDAXEXXZKZ-VDWQKOAOSA-N

物化性质

• 熔点：
  43-45 °C(Solvent: Chloroform)
• 沸点：
  346.4±9.0 °C(predicted)
• 密度：
  0.97±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  stemod-12-ene 在 lithium aluminium tetrahydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 4.0h， 生成 (+)-2-deoxy-stemodinone
  参考文献：
  名称：

  Kelly, Ronald B.; Harley, Mary Lou; Alward, Sandra J., Canadian Journal of Chemistry, 1983, vol. 61, p. 269 - 275

  摘要：

  DOI：
• 作为产物：
  描述：

  罗汉松酸 在 镍 吡啶 、 盐酸 、 氢氧化钾 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 methylsulfinyl carbanion 、 三氟化硼乙醚 、 sodium hydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 乙醇 、 二氯甲烷 、 水 、 二甲基亚砜 、 甲苯 为溶剂， 反应 176.15h， 生成 stemod-12-ene
  参考文献：
  名称：

  Kelly, Ronald B.; Harley, Mary Lou; Alward, Sandra J., Canadian Journal of Chemistry, 1983, vol. 61, p. 269 - 275

  摘要：

  DOI：

文献信息

• Biogenetic-Type Total Synthesis of (±)-2-Deoxystemodinone. Preliminary Communication
  作者：Alessandro Lupi、Maria Patamia、Ingeborg Grgurina、Rinaldo Marini Bettolo、Ornella Di Leo、Patrizia Gioia、Simonetta Autnaroli

  DOI：10.1002/hlca.19840670832

  日期：1984.12.19

  A biogenetic-type total synthesis of(±)-2-deoxystemodinone (1), by solvolytic rearrangement of the 1-methyl[2.2.2]oct-2-yl methanesulphonate 4, is described.

  描述了通过（1-）[2.2.2] oct-2-yl甲磺酸盐4的溶剂化重排的生物遗传型全合成（±）-2-脱氧硬脂酸二酮（1）。
• On the Construction of the C/D-Ring Systems of Aphidicolin and Stemodin: a Regio- and Stereospecific Synthesis of 17-Noraphidicolaii-16 one and 17-Norstemodan-16-one Preliminary Communication
  作者：Doriano Bravetti、Rinaldo Marini Bettolot、Alessandro Lupi

  DOI：10.1002/hlca.19820650139

  日期：1982.2.3

  A very simple regio- and stereospecific synthesis of 17-noraphidicolan-16-one and 17-norstemodan-16-one by solvolytic rearrangement of suitable bicyclo[2.2.2]--octenyl methanesulfonate is described.

  描述了通过合适的双环[2.2.2]-辛烯基甲磺酸盐的溶剂化重排非常简单的区域和立体有择地合成17-甲萘酚-16-和17-去甲甾烷-16-的方法。
• Investigation of the importance of the C-2 oxygen function in the transformation of stemodin analogues by Rhizopus oryzae ATCC 11145
  作者：Glenroy D.A. Martin、William F. Reynolds、Paul B. Reese

  DOI：10.1016/j.phytochem.2004.01.011

  日期：2004.3

  A new stemodinoside, stemodin-a-L-arabinofuranoside (5), was isolated from the plant Stemodia maritima. Incubation of stemodin (2) with Rhizopus oryzae ATCC 11145 gave 2alpha,7beta,13(S)-trihydroxystemodane (17) and 2alpha,3beta,13(S),16alpha-tetrahydroxystemodane (18) whilst stemodinone (8) afforded 6alpha,13(S)-dihydroxystemodan-2-one (19). The bioconversion of 2beta,13(S)-dihydroxystemodane (10) by the fungus yielded 2beta,7beta,13(S)-trihydroxystemodane (20) whereas stemod-12-en-2-one (9) provided 7beta,17-dihydroxystemod-12-en-2-one (21). The results provide useful information about the relationship between the functional groups of the substrates and their potential for bioconversion. (C) 2004 Elsevier Ltd. All rights reserved.
• The potential of Cyathus africanus for transformation of terpene substrates
  作者：Kayanne P. McCook、Avril R.M. Chen、William F. Reynolds、Paul B. Reese

  DOI：10.1016/j.phytochem.2012.06.018

  日期：2012.10

  The insecticidal sesquiterpenes cadina-4,10(15)-dien-3-one and aromadendr-1(10)-en-9-one were administered to the fungus Cyathus africanus ATCC 35853. Biotransformation of the former produced (4R)-9 alpha-hydroxycadin-10(15)-en-3-one, while the latter gave 2 beta-hydroxyaromadendr-1(10)-en-9-one, 2 alpha-hydroxyaromadendr-1(10)-en-9-one and 10 alpha-hydroxy-1 beta,2 beta-epoxyaromadendran-9-one. The bioconversion of santonin led to the production of two analogues, 11,13-dihydroxysantonin and the hitherto unreported 8 alpha,13-dihydroxysantonin, while cedrol yielded 3 beta,8 beta-dihydroxycedrane and 3 alpha,8 beta-dihydroxycedrane. Stemod-12-ene, a diterpene, was transformed to 2-oxostemar-13-ene, a hitherto unknown analogue with a rearranged carbon framework. When methyl betulonate, a triterpenoid belonging to the lupane family, was supplied to the fungus 18 alpha-ursane and 18 alpha-oleanane derivatives, namely 19 beta-hydroxy-3-oxo-18 alpha-oleanan-28-oic acid and 19 alpha-hydroxy-3-oxo-18 alpha-ursan-28-oic acids, were generated. There are no previous reports of fungal transformation of a triterpene in which a skeletal rearrangement occurred. All substrate administration experiments were done in the presence of the terpene cyclase inhibitor chlorocholine chloride (CCC), using the single phase - pulse feed method. (c) 2012 Elsevier Ltd. All rights reserved.
• Structures of stemodin and stemodinone
  作者：P. S. Manchand、J. D. White、Hal. Wright、Jon. Clardy

  DOI：10.1021/ja00789a060

  日期：1973.4