(R)-3-benzyloxymethyl-2-methylpent-4-en-2-ol | 861441-81-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-3-benzyloxymethyl-2-methylpent-4-en-2-ol
• 英文别名: (3R)-2-methyl-3-(phenylmethoxymethyl)pent-4-en-2-ol
• CAS: 861441-81-8
• 化学式: C₁₄H₂₀O₂
• 分子量: 220.312
• InChiKey: ICEYILRMIMBMAI-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  16
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 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)-3-benzyloxymethyl-2-methylpent-4-en-2-ol 在 三氟甲磺酸 、 sodium hydride 作用下， 以 二氯甲烷 为溶剂， 反应 30.0h， 生成
  参考文献：
  名称：

  Stereoselective 4-Benzyloxybut-2-enylation of Aldehydes via an Allyl-Transfer Reaction Using a Chiral Allyl Donor

  摘要：

  A direct and highly stereoselective (E)-4-benzyloxybut-2-enylation of aldehydes was successfully carried out to give 5-benzyloxyhomoallylic alcohol (11) via an allyl-transfer reaction using a chiral allyl donor (10). The chiral allyl donor (10) was prepared by catalytic Sharpless asymmetric epoxidation of 3-methylbut-2-en-l-ol, followed by a stereospecific vinyl Grignard reaction of the epoxide in the presence of CuBr and selective benzylation of the primary alcohol of diol.

  DOI：

  10.1021/ol050890t
• 作为产物：
  描述：

  异戊烯醇 在 叔丁基过氧化氢 titanium(IV) isopropylate 、 copper(I) bromide dimethylsulfide complex 、 二甲基硫 、 4 A molecular sieve 、 (-)-diethyl tartrate 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.5h， 生成 (R)-3-benzyloxymethyl-2-methylpent-4-en-2-ol
  参考文献：
  名称：

  Stereoselective 4-Benzyloxybut-2-enylation of Aldehydes via an Allyl-Transfer Reaction Using a Chiral Allyl Donor

  摘要：

  A direct and highly stereoselective (E)-4-benzyloxybut-2-enylation of aldehydes was successfully carried out to give 5-benzyloxyhomoallylic alcohol (11) via an allyl-transfer reaction using a chiral allyl donor (10). The chiral allyl donor (10) was prepared by catalytic Sharpless asymmetric epoxidation of 3-methylbut-2-en-l-ol, followed by a stereospecific vinyl Grignard reaction of the epoxide in the presence of CuBr and selective benzylation of the primary alcohol of diol.

  DOI：

  10.1021/ol050890t

文献信息

• Stereoselective 4-Benzyloxybut-2-enylation of Aldehydes via an Allyl-Transfer Reaction Using a Chiral Allyl Donor
  作者：Siddiqi M. Shafi、Jingyu Chou、Kazuhide Kataoka、Junzo Nokami

  DOI：10.1021/ol050890t

  日期：2005.7.1

  A direct and highly stereoselective (E)-4-benzyloxybut-2-enylation of aldehydes was successfully carried out to give 5-benzyloxyhomoallylic alcohol (11) via an allyl-transfer reaction using a chiral allyl donor (10). The chiral allyl donor (10) was prepared by catalytic Sharpless asymmetric epoxidation of 3-methylbut-2-en-l-ol, followed by a stereospecific vinyl Grignard reaction of the epoxide in the presence of CuBr and selective benzylation of the primary alcohol of diol.