(R)-7-methyloct-6-ene-1,3-diol | 93041-02-2

• 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: (R)-7-methyloct-6-ene-1,3-diol
• 英文别名: (3R)-1,2-dihydroxy-7-methyloct-6-ene；(3R)-7-methyloct-6-ene-1,3-diol
• CAS: 93041-02-2
• 化学式: C₉H₁₈O₂
• 分子量: 158.241
• InChiKey: IJKWYGLUJSTESM-SECBINFHSA-N

物化性质

• 沸点：
  276.5±20.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  11
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 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：

  (R)-7-methyloct-6-ene-1,3-diol 在 吡啶 、 sodium hydroxide 、 copper(l) iodide 、 三乙胺 作用下， 以 吡啶 、 甲醇 为溶剂， 反应 6.67h， 生成 (S)-(-)-β-香茅醇
  参考文献：
  名称：

  Convenient synthesis of (S)-citronellol of high optical purity

  摘要：

  DOI：

  10.1021/jo00201a027
• 作为产物：
  描述：

  (R)-3-羟基-7-甲基-6-辛烯酸甲酯 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 1.0h， 以76%的产率得到(R)-7-methyloct-6-ene-1,3-diol
  参考文献：
  名称：

  Tuning Stereoselection in Tethered Biginelli Condensations. Synthesis of cis- or trans-1-Oxo- and 1-Iminohexahydropyrrolo[1,2-c]pyrimidines

  摘要：

  Stereoselection in tethered Biginelli condensations can be tuned to give either the cia or trans stereoisomer of 1-oxohexahydropyrrolo[1,2-c]pyrimidine and 1-iminohexahydropyrrolo[1,2-c]pyrimidine products (see eq 1). With substrates having urea and N-sulfonylguanidine functionality (Schemes 2 and 4), cis stereoselection (4-7:1) is observed when the condensation is accomplished under Knoevenagel conditions, while trans stereoselection (4-20:1) is observed when the condensation is carried out in the presence of polyphosphate ester (PPE). Under both conditions, steroselectivity is highest in the N-sulfonylguanidine series. With substrates bearing a basic guanidine unit, the trans product is formed exclusively under Knoevenagel conditions (Scheme 3).

  DOI：

  10.1021/jo981972g

文献信息

• Method for improved chemical synthesis of guanidinium alkaloids
  申请人：Overman E. Larry

  公开号：US20050239804A1

  公开（公告）日：2005-10-27

  Improved methods for convergent, total enantioselective synthesis of guanidinium alkaloid compounds including ones having cis- or -trans-1-oxo-and 1-iminohexahydropyrrolo [1,2c]pyrimidine units including, 13,14,15-isocrambescidin 800, crambescidin 800 and ptilomycalin A, for use as therapeutic agents having antifungal and/or antiviral and/or antitumor activity are provided. Methods for preparing novel pentacyclic intermediates for the preparation of the crambescidin/ptilomycalin family of guanidinium alkaloids and congeners are also disclosed.

  提供了改进的方法，用于收敛、完全对映选择性合成葫芦啶生物碱化合物，包括具有顺式或反式1-氧基和1-亚氨基六氢吡咯并[1,2c]嘧啶单元的化合物，包括13,14,15-异克林贝斯酸800、克林贝斯酸800和莫纳霉素A，用作具有抗真菌和/或抗病毒和/或抗肿瘤活性的治疗剂。还公开了制备新的五环中间体的方法，用于制备克林贝斯酸/莫纳霉素家族的葫芦啶生物碱及其同系物。
• JPS60190737A
  申请人：——

  公开号：JPS60190737A

  公开（公告）日：1985-09-28
• Convenient synthesis of (S)-citronellol of high optical purity
  作者：Masahiro Hirama、Takeshi Noda、Sho Ito

  DOI：10.1021/jo00201a027

  日期：1985.1
• Tuning Stereoselection in Tethered Biginelli Condensations. Synthesis of <i>cis</i>- or <i>trans</i>-1-Oxo- and 1-Iminohexahydropyrrolo[1,2-<i>c</i>]pyrimidines
  作者：Andrew I. McDonald、Larry E. Overman

  DOI：10.1021/jo981972g

  日期：1999.3.1

  Stereoselection in tethered Biginelli condensations can be tuned to give either the cia or trans stereoisomer of 1-oxohexahydropyrrolo[1,2-c]pyrimidine and 1-iminohexahydropyrrolo[1,2-c]pyrimidine products (see eq 1). With substrates having urea and N-sulfonylguanidine functionality (Schemes 2 and 4), cis stereoselection (4-7:1) is observed when the condensation is accomplished under Knoevenagel conditions, while trans stereoselection (4-20:1) is observed when the condensation is carried out in the presence of polyphosphate ester (PPE). Under both conditions, steroselectivity is highest in the N-sulfonylguanidine series. With substrates bearing a basic guanidine unit, the trans product is formed exclusively under Knoevenagel conditions (Scheme 3).