(R)-benzyloxy-7-methyloct-6-en-3-ol | 221493-07-8

• 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: (R)-benzyloxy-7-methyloct-6-en-3-ol
• 英文别名: (3R)-7-methyl-1-phenylmethoxyoct-6-en-3-ol
• CAS: 221493-07-8
• 化学式: C₁₆H₂₄O₂
• 分子量: 248.365
• InChiKey: SEYUFDYWFHOVOA-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R)-benzyloxy-7-methyloct-6-en-3-ol 在 lithium aluminium tetrahydride 、 三(2-氯乙基)胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 乙醚 、 异丙醇 、 甲苯 为溶剂， 反应 4.0h， 生成 (S)-1-benzyloxy-7-methyl-3-ureido-6-octene
  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
• 作为产物：
  描述：

  (R)-3-羟基-7-甲基-6-辛烯酸甲酯 在 lithium aluminium tetrahydride 、 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 (R)-benzyloxy-7-methyloct-6-en-3-ol
  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。
• HEXAHYDROPYRROLO[1,2-C]PYRIMIDINES AS ANTIVIRAL, ANTIFUNGAL AND/OR ANTITUMOR AGENTS
  申请人：THE REGENTS OF THE UNIVERSITY OF CALIFORNIA

  公开号：EP1204666A1

  公开（公告）日：2002-05-15
• [EN] HEXAHYDROPYRROLO[1,2-C]PYRIMIDINES AS ANTIVIRAL, ANTIFUNGAL AND/OR ANTITUMOR AGENTS<br/>[FR] HEXAHYDROPYRROLO[1,2-C]PYRIMIDINES UTILISEES EN TANT QU'AGENTS ANTIVIRAUX, ANTIFONGIQUES ET/OU ANTITUMORAUX
  申请人：UNIV CALIFORNIA

  公开号：WO2001000626A1

  公开（公告）日：2001-01-04

  Improved methods for convergent, total enantioselective synthesis of guanidinium alkaloid compounds including ones having cis- or -trans-1-oxo- and 1-iminohexahydropyrrolo[1,2-c]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.
• 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).