(3R)-tridec-12-ene-1,3-diol | 532929-13-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (3R)-tridec-12-ene-1,3-diol
• CAS: 532929-13-8
• 化学式: C₁₃H₂₆O₂
• 分子量: 214.348
• InChiKey: FNCCTESOCKJRGF-CYBMUJFWSA-N

物化性质

• 沸点：
  313.8±10.0 °C(Predicted)
• 密度：
  0.917±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  15
• 可旋转键数：
  11
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (3R)-tridec-12-ene-1,3-diol 在 咪唑 、 sodium periodate 、 Wilkinson's catalyst 、 四氧化锇 、 正丁基锂 、 D(+)-10-樟脑磺酸 、 氢气 、 二异丁基氢化铝 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 、 苯 为溶剂， -78.0~60.0 ℃ 、13.33 kPa 条件下， 反应 43.22h， 生成 (2R,8R,20R)-2-benzyloxy-22-(tert-butyldiphenylsilanyloxy)-20-(4-methoxybenzyloxy)docosan-8-ol
  参考文献：
  名称：

  Synthetic Studies on Macroviracin A:  A Rapid Construction of C₄₂ Macrocyclic Dilactone Corresponding to the Core

  摘要：

  The C-2-symmetric macrodiolide core 2 of an antiviral agent, macroviracin A (1), was constructed in a single step by the intermolecular macrodimerization of C-22-hydroxy carboxylic acid 3 with 2-chloro-1,3-dimethylimidazolinium chloride and DMAP in the presence of sodium hydride (NaH). The use of potassium hydride instead of NaH caused the intramolecular cyclization, predominantly providing the corresponding monomer 26. The acid 3 was synthesized through a series of reactions such as the coupling reaction of acetylene 5 and oxirane 6, stereoselective glycosidation with the trichloroacetimidate method, and Jones oxidation.

  DOI：

  10.1021/jo0496392
• 作为产物：
  描述：

  10-十一烯醛 在 4 A molecular sieve titanium(IV) isopropylate 、 叔丁基过氧化氢 、 sodium hydride 、 二异丁基氢化铝 、 (-)-diethyl tartrate 、 红铝 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 (3R)-tridec-12-ene-1,3-diol
  参考文献：
  名称：

  Determination of Absolute Structure of Macroviracins by Chemical Synthesis

  摘要：

  The relative and absolute configurations of macroviracins have been established by the stereocontrolled synthesis of methyl ester 2a of the C-22 carboxylic acid, a constitutive fatty acid of macroviracin A (1), and their comparison to a sample 2 derived from the natural product 1.

  DOI：

  10.1021/ol034338k

文献信息

• Determination of Absolute Structure of Macroviracins by Chemical Synthesis
  作者：Shunya Takahashi、Moritoshi Hosoya、Hiroyuki Koshino、Tadashi Nakata

  DOI：10.1021/ol034338k

  日期：2003.5.1

  The relative and absolute configurations of macroviracins have been established by the stereocontrolled synthesis of methyl ester 2a of the C-22 carboxylic acid, a constitutive fatty acid of macroviracin A (1), and their comparison to a sample 2 derived from the natural product 1.
• Synthetic Studies on Macroviracin A:  A Rapid Construction of C₄₂ Macrocyclic Dilactone Corresponding to the Core
  作者：Shunya Takahashi、Kazunori Souma、Ruri Hashimoto、Hiroyuki Koshino、Tadashi Nakata

  DOI：10.1021/jo0496392

  日期：2004.6.1

  The C-2-symmetric macrodiolide core 2 of an antiviral agent, macroviracin A (1), was constructed in a single step by the intermolecular macrodimerization of C-22-hydroxy carboxylic acid 3 with 2-chloro-1,3-dimethylimidazolinium chloride and DMAP in the presence of sodium hydride (NaH). The use of potassium hydride instead of NaH caused the intramolecular cyclization, predominantly providing the corresponding monomer 26. The acid 3 was synthesized through a series of reactions such as the coupling reaction of acetylene 5 and oxirane 6, stereoselective glycosidation with the trichloroacetimidate method, and Jones oxidation.