(-)-(2S,5S)-5-isopropyl-2-methyl-2-(2-oxoethyl)methylenecyclopentane | 117152-55-3

• 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: (-)-(2S,5S)-5-isopropyl-2-methyl-2-(2-oxoethyl)methylenecyclopentane
• 英文别名: 2-[(1S,3S)-1-methyl-2-methylidene-3-propan-2-ylcyclopentyl]acetaldehyde
• CAS: 117152-55-3
• 化学式: C₁₂H₂₀O
• 分子量: 180.29
• InChiKey: QJNIAMPPRFSOIN-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-(2S,5S)-5-isopropyl-2-methyl-2-(2-oxoethyl)methylenecyclopentane 在 吡啶 、 lithium aluminium tetrahydride 、 高氯酸 、 乙酸酐 、 magnesium 、 pyridinium chlorochromate 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 14.58h， 生成 (-)-dauca-4,8-diene
  参考文献：
  名称：

  Mehta, Goverdhan; Krishnamurthy, Nacharaju, Synthetic Communications, 1988, vol. 18, # 11, p. 1267 - 1274

  摘要：

  DOI：
• 作为产物：
  描述：

  甜橙提取物 在 sodium tetrahydroborate 、 mercury(II) diacetate 作用下， 以 甲醇 为溶剂， 生成 (-)-(2S,5S)-5-isopropyl-2-methyl-2-(2-oxoethyl)methylenecyclopentane
  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

• Claisen-based strategy for the de novo construction of basmane diterpenes. Enantiospecific synthesis of (+)-7,8-epoxy-2-basmen-6-one
  作者：Ho Jung Kang、Leo A. Paquette

  DOI：10.1021/ja00164a078

  日期：1990.4

  Synthese du compose du titre a partir d'isopropyl 3 methyl-1 methylene-2 cyclopentaneacetaldehyde via une transposition Claisen d'isopropyl-7 hexahydro methyl-4a methylene-2 propenyl-7a cyclopenta [b] pyranne en isopropyl-1 dimethyl-3a,8 hexahydro cyclopentacyclooctenone-6

  [b]吡喃烯异丙基-1甲基-2环戊烷乙醛通过转位Claisen d'isopropyl-7 hexahydromethyl-4a methylene-2 propenyl-7a cyclopenta [b] pyranne en isopropyl-1二甲基-3a， 8 六氢环戊环辛烯酮-6
• 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).
• Enantiospecific total synthesis of 6-epi-(−)-hamigeran B. Intramolecular Heck reaction in a sterically constrained environment
  作者：Goverdhan Mehta、Harish M. Shinde

  DOI：10.1016/s0040-4039(03)01754-4

  日期：2003.9

  An enantiospecific approach, emanating from the abundantly available chiron R-(+)-limonene, to the biologically potent, novel marine natural products, the hamigerans has been developed in which an intramolecular Heck coupling between aryl triflates and an alkene serves as the pivotal step. Following this strategy, a synthesis of (-)-6-epi-hamigeran B has been accomplished. (C) 2003 Elsevier Ltd. All rights reserved.
• PAQUETTE, LEO A.;KANG, HO-JUNG, J. AMER. CHEM. SOC., 113,(1991) N, C. 2610-2621
  作者：PAQUETTE, LEO A.、KANG, HO-JUNG

  DOI：——

  日期：——
• MEHTA, GOVERDHAN;KRISHNAMURTHY, NACHARAJU;RAO, KARRA SRINIVAS, J. AMER. CHEM. SOC., 113,(1991) N9, C. 5765-5775
  作者：MEHTA, GOVERDHAN、KRISHNAMURTHY, NACHARAJU、RAO, KARRA SRINIVAS

  DOI：——

  日期：——