(2S,5S)-5-isopropyl-2-methyl-2-(3-carbetoxy-2-hydroxypropyl)methylenecyclopentane | 117133-37-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (2S,5S)-5-isopropyl-2-methyl-2-(3-carbetoxy-2-hydroxypropyl)methylenecyclopentane
• 英文别名: ethyl 3-hydroxy-4-[(1S,3S)-1-methyl-2-methylidene-3-propan-2-ylcyclopentyl]butanoate
• CAS: 117133-37-6；117181-70-1
• 化学式: C₁₆H₂₈O₃
• 分子量: 268.397
• InChiKey: LOLSWUOMQKIWPQ-DSUHRAPHSA-N

物化性质

• 沸点：
  360.2±15.0 °C(predicted)
• 密度：
  0.98±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.32
• 重原子数：
  19.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  46.53
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (2S,5S)-5-isopropyl-2-methyl-2-(3-carbetoxy-2-hydroxypropyl)methylenecyclopentane 在 吡啶 、 叔丁基过氧化氢 、 lithium aluminium tetrahydride 、 selenium(IV) oxide 、 C₁₀H₈^(1-)Na⁽¹⁺⁾ 、 四丁基氟化铵 、 4-甲基苯磺酸吡啶 、 四氯化锡 、 sodium hydride 、 二异丁基氢化铝 、 pyridinium chlorochromate 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 乙醚 、 二氯甲烷 为溶剂， 生成 (+)-dolasta-1(15),7,9-trien-14-ol
  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
• 作为产物：
  描述：

  甜橙提取物 在 sodium tetrahydroborate 、 mercury(II) diacetate 、 锌 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 生成 (2S,5S)-5-isopropyl-2-methyl-2-(3-carbetoxy-2-hydroxypropyl)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

• 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;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：——
• MEHTA, GOVERDHAN;KRISHNAMURTHY, NACHARAJU, TETRAHEDRON LETT., 28,(1987) N 47, 5945-5948
  作者：MEHTA, GOVERDHAN、KRISHNAMURTHY, NACHARAJU

  DOI：——

  日期：——