(1S,3S,4R,6R,7R)-4-Isopropyl-1-methyl-7-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-bicyclo[4.1.0]heptan-3-ol | 213544-77-5

• 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: (1S,3S,4R,6R,7R)-4-Isopropyl-1-methyl-7-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-bicyclo[4.1.0]heptan-3-ol
• 英文别名: (1S,3S,4R,6R,7R)-1-methyl-7-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-4-propan-2-ylbicyclo[4.1.0]heptan-3-ol
• CAS: 213544-77-5
• 化学式: C₁₇H₃₀O₃
• 分子量: 282.423
• InChiKey: LHFCHWQRBRIXHK-SUJAAXHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-(+)-α-甲氧基-α-(三氟甲基)苯乙酸 、 (1S,3S,4R,6R,7R)-4-Isopropyl-1-methyl-7-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-bicyclo[4.1.0]heptan-3-ol 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以57%的产率得到(R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (1S,3S,4R,6R,7R)-4-isopropyl-1-methyl-7-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-bicyclo[4.1.0]hept-3-yl ester
  参考文献：
  名称：

  Absolute stereostructure of carabrane-type sesquiterpene and vasorelaxant-active sesquiterpenes from Zedoariae Rhizoma

  摘要：

  The aqueous acetone extract of Zedoariae Rhizoma was found to show inhibitory effects on contractions induced by high concentrations of potassium cation (K+) in isolated rat aortic strips. From the extract, two new carabrane-type sesquiterpenes, curcarabranols A and B, were isolated together with a few carabrane-type sesquiterpenes, such as curcumenone and 4S-dihydrocurcumenone. Their absolute stereostructures were determined on the basis of chemical and physicochemical evidence, which included the application of the modified Mosher's method and chemical conversion from curcumenone to curcarabranols A and B. In addition, several sesquiterpenes and diaryl-heptanoids (e.g. germacrone, glechomanolide, isocurucmenol, beta -eudesmol, and beta -dictyopterol) showed potent inhibitory effects on contractions induced by high concentrations of K+ in isolated rat aortic strips (inhibition > 80% at 100 muM), while they did not inhibit norepinephrine-induced contractions, so that the vasorelaxant activities of these sesquiterpenes were presumed to be dependent on their calcium channel-blocking activity. (C) 2001 Elsevier Science Ltd. AE rights reserved.

  DOI：

  10.1016/s0040-4020(01)00828-6
• 作为产物：
  描述：

  (1S,6R,7R)-1-methyl-7-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-4-propan-2-ylidenebicyclo[4.1.0]heptan-3-one 在 palladium hydroxide - carbon sodium tetrahydroborate 、 氢气 作用下， 以 甲醇 为溶剂， 生成 (1S,3S,4R,6R,7R)-4-Isopropyl-1-methyl-7-[2-(2-methyl-[1,3]dioxolan-2-yl)-ethyl]-bicyclo[4.1.0]heptan-3-ol
  参考文献：
  名称：

  Absolute Stereostructures of Carabrane-Type Sesquiterpenes, Curcumenone, 4S-Dihydrocurcumenone, and Curcarabranols A and B: Vasorelaxant Activity of Zedoary Sesquiterpenes.

  摘要：

  从莪术中分离出了新的莪术酚 A 和 B，以及两种已知的莪术酮和 4S- 二氢莪术酮。根据物理化学和化学证据确定了这些石榴烯类倍半萜的绝对立体结构。研究发现，包括 4S- 二氢莪术酮和莪术醇 A 和 B 在内的泽泻烯类倍半萜能抑制高浓度 K+ 在离体大鼠主动脉条带上引起的收缩。

  DOI：

  10.1248/cpb.46.1186