(+)-2-deoxy-stemodinone | 41703-77-9

• 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: (+)-2-deoxy-stemodinone
• 英文别名: (+)-2-desoxystemodinone；13(S)-hydroxystemodane；Desoxystemodin；(1R,2S,7S,10S,12S,13S)-2,6,6,13-tetramethyltetracyclo[10.3.1.01,10.02,7]hexadecan-13-ol
• CAS: 41703-77-9
• 化学式: C₂₀H₃₄O
• 分子量: 290.489
• InChiKey: ODCPNBCPLWJVQI-WKSOIMLMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  (+)-2-deoxy-stemodinone 在 吡啶 、 三氯氧磷 作用下， 生成 stemod-12-ene
  参考文献：
  名称：

  Structures of stemodin and stemodinone

  摘要：

  DOI：

  10.1021/ja00789a060
• 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 、 lithium aluminium tetrahydride 、 methylsulfinyl carbanion 、 三氟化硼乙醚 、 sodium hydride 、 对甲苯磺酸 、 间氯过氧苯甲酸 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 、 苯 为溶剂， 反应 180.15h， 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：

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）。
• 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.
• Construction of the Stemodane Nucleus by a Hydroxyl-Directed Intramolecular Ene Reaction. Total Synthesis of (.+-.)-2-Desoxystemodinone
  作者：James D. White、Todd C. Somers

  DOI：10.1021/ja00101a012

  日期：1994.11

  A synthesis of the diterpene 2-desoxystemodinone was completed from the known tricyclic ketone 9 in eight steps and 35% overall yield. The key step involved a thermal intramolecular ene reaction of alpha-hydroxy aldehyde 21 which led to 24 in 94% yield. By contrast, a Lewis acid-catalyzed ene reaction of 21 gave oxetane 25 as the major product. The pivotal role of the hydroxyl substituent of 21 in facilitating the ene reaction was demonstrated and is rationalized by a hydrogen bond which orients the carbonyl in a favorable conformation for rearrangement.
• Total synthesis of (.+-.)-2-desoxystemodinone. A novel hydroxyl-assisted, intramolecular ene reaction
  作者：James D. White、Todd C. Somers

  DOI：10.1021/ja00248a065

  日期：1987.7
• Kelly, Ronald B.; Harley, Mary Lou; Alward, Sandra J., Canadian Journal of Chemistry, 1983, vol. 61, p. 269 - 275
  作者：Kelly, Ronald B.、Harley, Mary Lou、Alward, Sandra J.、Rej, Rabindra N.、Gowda, Gopala、et al.

  DOI：——

  日期：——