(2R)-2,4-Dimethylpent-4-en-1-ol | 147753-92-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R)-2,4-Dimethylpent-4-en-1-ol
• CAS: 147753-92-2
• 化学式: C₇H₁₄O
• 分子量: 114.188
• InChiKey: ZYKOKYNWPPTFDF-SSDOTTSWSA-N

物化性质

• 沸点：
  163.2±9.0 °C(Predicted)
• 密度：
  0.834±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  8
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (2R)-2,4-Dimethylpent-4-en-1-ol 在 咪唑 、 thexylborane 、 双氧水 、 碳酸氢钠 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (2S,4R)-5-(tert-butyl(dimethyl)silyloxy)-2,4-dimethyl-1-pentanol
  参考文献：
  名称：

  A sex pheromone isolated from Macrocentrus grandii: absolute stereochemistry determination and implications

  摘要：

  DOI：

  10.1021/jo00062a048
• 作为产物：
  描述：

  (R)-1-[(2',4'-dimethylpent-4'-enyloxy)methyl]-4-methoxybenzene 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 12.0h， 生成 (2R)-2,4-Dimethylpent-4-en-1-ol
  参考文献：
  名称：

  Asymmetric Sharpless Dihydroxylation Reaction of Chiral Bishomoallylic Alcohols: Application to the Synthesis of the C1–C10–C5 Fragment of FR225654

  摘要：

  Toward the synthesis of FR225654, an antidiabetic natural product, the Sharpless asymmetric dihydroxylation of chiral bishomoallylic alcohols, never reported in the literature, was examined. Employing the pyrimidine class of ligands, a high level of matched diastereoselectivity was obtained. An application to the stereoselective synthesis of the C1-C10-C5 fragment of FR225654 was performed.

  DOI：

  10.1055/s-0033-1340164

文献信息

• Evolution of a Total Synthesis of (−)-Kendomycin Exploiting a Petasis−Ferrier Rearrangement/Ring-Closing Olefin Metathesis Strategy
  作者：Amos B. Smith、Eugen F. Mesaros、Emmanuel A. Meyer

  DOI：10.1021/ja060369+

  日期：2006.4.1

  stereocontrolled total synthesis of (-)-kendomycin (1) has been achieved. The synthesis proceeds with a longest linear sequence of 21 steps, beginning with commercially available 2,4-dimethoxy-3-methylbenzaldehyde (12). Highlights of the synthesis include an effective Petasis-Ferrier union/rearrangement tactic to construct the sterically encumbered tetrahydropyran ring, a ring-closing metathesis to generate

  已经实现了 (-)-kendomycin (1) 的收敛立体控制全合成。合成以最长的 21 步线性序列进行，从市售的 2,4-二甲氧基-3-甲基苯甲醛 (12) 开始。合成的亮点包括有效的 Petasis-Ferrier 结合/重排策略以构建空间位阻四氢吡喃环、闭环复分解以生成 C(4a-13-20a) 大环、有效的环氧化/脱氧序列以异构化 C (13,14) 烯烃和仿生醌-甲基-乳糖醇组装完成合成。
• Total Synthesis of (−)-Kendomycin Exploiting a Petasis−Ferrier Rearrangement/Ring-Closing Olefin Metathesis Synthetic Strategy
  作者：Amos B. Smith、Eugen F. Mesaros、Emmanuel A. Meyer

  DOI：10.1021/ja051420x

  日期：2005.5.1

  The total synthesis of (-)-kendomycin (1), a novel macrocyclic polyketide with antibacterial and antitumor activity, was achieved in 21 steps (longest linear sequence) exploiting an effective Petasis-Ferrier union/rearrangement tactic to construct the tetrahydropyran ring, a ring-closing metathesis to generate the macrocycle, and a biomimetic quinone-methide-lactol assembly.

  (-)-kendomycin (1) 是一种具有抗菌和抗肿瘤活性的新型大环聚酮化合物，通过 21 个步骤（最长的线性序列）实现了全合成，利用有效的 Petasis-Ferrier 结合/重排策略构建了四氢吡喃环，闭环复分解产生大环，和仿生醌-甲基-乳糖组装。
• Zirconium-catalyzed asymmetric carboalumination (ZACA reaction) of 1,4-dienes
  作者：Ze Tan、Bo Liang、Shouquan Huo、Ji-cheng Shi、Ei-ichi Negishi

  DOI：10.1016/j.tetasy.2006.01.017

  日期：2006.2

  group, readily undergo the ZACA reaction with Me3Al and higher alkylalanes in a 1:1 molar ratio in the presence of a catalytic amount (1–5 mol %) of bis[(1-neomenthyl)indenyl]zirconium dichloride in good yields and in good enantioselectivity (70–92% ee), thereby providing an efficient and convenient route to various alkene-containing chiral natural products. Only the reaction of the parent 1,4-pentadiene

  在催化量（1-5 mol％）的存在下，具有末端乙烯基（H 2 CCH）基团的各种取代的1,4-二烯易于与Me 3 Al和高级烷基丙烯按1：1摩尔比进行ZACA反应）双[（1-新薄荷基）茚基]二氯化锆，收率高，对映选择性好（70-92％ee），从而为各种含烯烃的手性天然产物提供了一种有效而便捷的途径。仅母体1，4-戊二烯的反应伴随着大量的外消旋化。
• A sex pheromone isolated from Macrocentrus grandii: absolute stereochemistry determination and implications
  作者：Injae Shin、Hui Qiang Zhou、Nanette Loida S. Que、Hung Wen Liu、Paul D. Swedenborg、Richard L. Jones

  DOI：10.1021/jo00062a048

  日期：1993.5
• Asymmetric Sharpless Dihydroxylation Reaction of Chiral Bishomoallylic Alcohols: Application to the Synthesis of the C1–C10–C5 Fragment of FR225654
  作者：Marie-Isabelle Lannou、Shabbair Mohammad、Sabrina Dhambri、Didier Gori、Carine Vaxelaire、Geoffroy Sorin、Janick Ardisson

  DOI：10.1055/s-0033-1340164

  日期：——

  Toward the synthesis of FR225654, an antidiabetic natural product, the Sharpless asymmetric dihydroxylation of chiral bishomoallylic alcohols, never reported in the literature, was examined. Employing the pyrimidine class of ligands, a high level of matched diastereoselectivity was obtained. An application to the stereoselective synthesis of the C1-C10-C5 fragment of FR225654 was performed.