(-)-8-isopropyl-1(S)-methylbicyclo<5.3.0>dec-7(8)-en-3-one | 117182-78-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (-)-8-isopropyl-1(S)-methylbicyclo<5.3.0>dec-7(8)-en-3-one
• 英文别名: (3aS)-3a-methyl-1-propan-2-yl-2,3,4,6,7,8-hexahydroazulen-5-one
• CAS: 117182-78-2
• 化学式: C₁₄H₂₂O
• 分子量: 206.328
• InChiKey: NURGKTBTOZRZMJ-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  17.07
• 氢给体数：
  0.0
• 氢受体数：
  1.0

反应信息

• 作为反应物：
  描述：

  (-)-8-isopropyl-1(S)-methylbicyclo<5.3.0>dec-7(8)-en-3-one 以80%的产率得到
  参考文献：
  名称：

  MEHTA, GOVERDHAN;KRISHNAMURTHY, NACHARAJU, TETRAHEDRON LETT., 28,(1987) N 47, 5945-5948

  摘要：

  DOI：
• 作为产物：
  描述：

  甜橙提取物 在 sodium tetrahydroborate 、 重铬酸吡啶 、 高氯酸 、 mercury(II) diacetate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 (-)-8-isopropyl-1(S)-methylbicyclo<5.3.0>dec-7(8)-en-3-one
  参考文献：
  名称：

  An enantioselective approach to dolastane diterpenes. Total synthesis of marine natural products (+)-isoamijiol and (+)-dolasta-1(15),7,9-trien-14-OL

  摘要：

  DOI：

  10.1016/s0040-4039(01)81097-2

文献信息

• Enantioselective approach to isodaucane sesquiterpenes. Total synthesis of (+)-aphanamol-I and (+)-2-oxo-isodauc-5-en-12-al
  作者：Goverdhan Mehta、Nacharaju Krishnamurthy、Srinivas Rao Karra

  DOI：10.1039/c39890001299

  日期：——

  A general approach to isodaucane sesquiterpenes from (R)-(+)-limonene, resulting in the total synthesis of (+)-aphanamol-I (3) and (+)-2-oxo-isodauc-5-en-12-al (5), is described.

  从（R）-（+）-柠檬烯制异七烷倍半萜的通用方法，导致（+）-甲氨酚-I（3）和（+）-2-氧代-异豆基-5-烯-12-的全合成描述了al（5）。
• An oxy-cope rearrangement route for the enantioselective construction of 5,11-fused framework of dolabellane diterpenes
  作者：Goverdhan Mehta、Srinivas Rao Karra、Nacharaju Krishnamurthy

  DOI：10.1016/s0040-4039(00)77026-2

  日期：1994.4

  A sequence for generating the dolabellane diterpene framework from (R)-limonene is delineated.

  描绘了从（R）-柠檬烯生成多标签二萜二萜骨架的序列。
• Terpenoids to terpenoids: enantioselective construction of 5,6-, 5,7-, and 5,8-fused bicyclic systems. Application to the total synthesis of isodaucane sesquiterpenes and dolastane diterpenes
  作者：Goverdhan Mehta、Nacharaju Krishnamurthy、Srinivas Rao Karra

  DOI：10.1021/ja00015a034

  日期：1991.7

  The prevalence of a C12 common core (10) in C15-C30 terpenoids has been recognized. Construction of two ''chirons'' ((-)-11 and (-)-12a,b), corresponding to 10, from abundantly available (R)-(+)-limonene has been achieved through diastereoselective [3s.3s] sigmatropic processes 16 --> 11 and 19 --> 12, respectively. Chirons 11 and 12 have been successfully annulated to bicyclic hydrindanones 21, 23, and 30, hydrazulenoids 31-33, and 5,8-fused system 42 through methodologies that are short and practical. Thus, these enantiomerically pure bicyclics are available as advanced building blocks for higher terpene synthesis. One of the hydrazulenoids ((-)-31) has been elaborated to isodaucane sesquiterpenes (+)-aphanamol I (2) and (+)-2-oxoisodauc-5-en-12-al (46) through a novel restructuring protocol (31 --> 50). The stereo- and enantioselective synthesis reported here has established the absolute stereochemistry of isodaucane sesquiterpenes. The hydrazulenoid (-)-31 has also been deployed for the first enantioselective synthesis of oxygenated dolastane diterpenes (+)-isoamijiol (63) and (+)-dolasta-1(15),7,9-trien-14-ol (64). The key step in this venture was the stereoselective annulation of a six-membered ring through radical-induced alkyne-carbonyl cyclization (67 --> 68).
• Mehta, Goverdhan; Karra, Srinivasa Rao, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1989, vol. 28, # 1-11, p. 367 - 368
  作者：Mehta, Goverdhan、Karra, Srinivasa Rao

  DOI：——

  日期：——
• MEHTA, GOVERDHAN;KRISHNAMURTHY, NACHARAJU;KARRA, SRINIVAS RAO, J. CHEM. SOC. CHEM. COMMUN.,(1989) N8, C. 1299-1300
  作者：MEHTA, GOVERDHAN、KRISHNAMURTHY, NACHARAJU、KARRA, SRINIVAS RAO

  DOI：——

  日期：——