1-(benzyloxy)hex-5-yn-3-ol | 251938-78-0

• 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: 1-(benzyloxy)hex-5-yn-3-ol
• 英文别名: 1-(Phenylmethoxy)-5-hexyn-3-ol；1-phenylmethoxyhex-5-yn-3-ol
• CAS: 251938-78-0
• 化学式: C₁₃H₁₆O₂
• 分子量: 204.269
• InChiKey: ZTDQZZZVVLKSLB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 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：

  1-(benzyloxy)hex-5-yn-3-ol 、 二甲醇缩甲醛 在 phosphorus pentoxide 作用下， 以 氯仿 为溶剂， 反应 5.0h， 以79%的产率得到3-(Methoxymethoxy)hex-5-ynoxymethylbenzene
  参考文献：
  名称：

  Stereoselective, Oxidative C−C Bond Coupling of Naphthopyran Induced by DDQ:  Stereocontrolled Total Synthesis of Deoxyfrenolicin

  摘要：

  A formal total synthesis of pyranonaphthoquinone natural product deoxyfrenolicin 1 is described. The key step in the synthesis involves the use of stereoselective 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-induced C-C bond coupling of the naphthopyran 10 with allyltriphenyltin to give exclusively 1,3 trans naphthopyran derivative 23, The naphthopyran 10 was obtained via oxa-Pictet-Spengler cyclization of substituted naphthalene 22, which was derived by regioselective benzannulation of chromium carbene complex 12 with acetylene 18, This newly developed synthetic route employing a tandem benzannulation/oxa-Pictet-Spengler cyclization/DDQ-induced coupling strategy should also be applicable to the synthesis of other pyranonaphthoquinone natural products such as kalafungin 4 and nanaomycin 5.

  DOI：

  10.1021/ol9909738
• 作为产物：
  描述：

  [(3-丁烯-1-基氧基)甲基]苯 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 16.67h， 生成 1-(benzyloxy)hex-5-yn-3-ol
  参考文献：
  名称：

  Stereoselective, Oxidative C−C Bond Coupling of Naphthopyran Induced by DDQ:  Stereocontrolled Total Synthesis of Deoxyfrenolicin

  摘要：

  A formal total synthesis of pyranonaphthoquinone natural product deoxyfrenolicin 1 is described. The key step in the synthesis involves the use of stereoselective 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-induced C-C bond coupling of the naphthopyran 10 with allyltriphenyltin to give exclusively 1,3 trans naphthopyran derivative 23, The naphthopyran 10 was obtained via oxa-Pictet-Spengler cyclization of substituted naphthalene 22, which was derived by regioselective benzannulation of chromium carbene complex 12 with acetylene 18, This newly developed synthetic route employing a tandem benzannulation/oxa-Pictet-Spengler cyclization/DDQ-induced coupling strategy should also be applicable to the synthesis of other pyranonaphthoquinone natural products such as kalafungin 4 and nanaomycin 5.

  DOI：

  10.1021/ol9909738

文献信息

• <i>C</i> ‐Propargylation Overrides <i>O</i> ‐Propargylation in Reactions of Propargyl Chloride with Primary Alcohols: Rhodium‐Catalyzed Transfer Hydrogenation
  作者：Tao Liang、Sang Kook Woo、Michael J. Krische

  DOI：10.1002/anie.201603575

  日期：2016.8

  The canonical SN2 behavior displayed by alcohols and activated alkyl halides in basic media (O‐alkylation) is superseded by a pathway leading to carbinol C‐alkylation under the conditions of rhodium‐catalyzed transfer hydrogenation. Racemic and asymmetric propargylations are described.

  在铑催化的转移加氢条件下，醇和活化的烷基卤化物在碱性介质（O-烷基化）中表现出的标准S N 2行为被导致甲醇C-烷基化的途径所取代。描述了外消旋和不对称的炔丙基化。
• Synthesis of 2,5-Disubstituted Dihydrofuran-3(2H)-ones via [2,3]-Sigmatropic Rearrangement of Oxonium Ylides Generated from α-Oxo Gold Carbenes
  作者：Jinsung Tae、Miyeon Han、Joohee Bae、Juhee Choi

  DOI：10.1055/s-0033-1339662

  日期：——

  oxonium ylides generated from α-oxo gold carbenes were discovered. An ­efficient synthetic method of 2,5-disubstituted dihydrofuran-3(2H)-ones via gold-catalyzed intermolecular oxidation of the allyl homopropargyl ethers with N-oxide was developed. And the synthetic utility of the current method has been proved by concise formal synthesis of (±)-kumausallene.

  发现了由α-氧代金卡宾产生的氧鎓叶立德的新型 [2,3]-σ 重排。开发了一种有效的 2,5-二取代二氢呋喃-3(2H)-酮的合成方法，通过金催化烯丙基高炔丙基醚与 N-氧化物的分子间氧化。并且通过(±)-kumausallene的简洁形式合成证明了当前方法的合成效用。
• Total Synthesis of (±)-5-Deoxystrigol via Reductive Carbon−Carbon Bond Formation
  作者：Mitsuru Shoji、Eriko Suzuki、Minoru Ueda

  DOI：10.1021/jo9002085

  日期：2009.5.15

  The total synthesis of 5-deoxystrigol was successfully carried out via the regioselective coupling reaction between the aluminum ate complex of an alkyne and an epoxide and the two reductive carbon−carbon bond formations in the presence of transition metals as key steps.

  通过脱氧炔烃和环氧化物的铝酸酯配合物与过渡金属存在下的两个还原碳-碳键形成之间的区域选择性偶联反应，成功地完成了5-脱氧雌三醇的合成，这是关键步骤。
• Stereoselective, Oxidative C−C Bond Coupling of Naphthopyran Induced by DDQ:  Stereocontrolled Total Synthesis of Deoxyfrenolicin
  作者：Yao-Chang Xu、Dan T. Kohlman、Sidney X. Liang、Chad Erikkson

  DOI：10.1021/ol9909738

  日期：1999.11.1

  A formal total synthesis of pyranonaphthoquinone natural product deoxyfrenolicin 1 is described. The key step in the synthesis involves the use of stereoselective 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ)-induced C-C bond coupling of the naphthopyran 10 with allyltriphenyltin to give exclusively 1,3 trans naphthopyran derivative 23, The naphthopyran 10 was obtained via oxa-Pictet-Spengler cyclization of substituted naphthalene 22, which was derived by regioselective benzannulation of chromium carbene complex 12 with acetylene 18, This newly developed synthetic route employing a tandem benzannulation/oxa-Pictet-Spengler cyclization/DDQ-induced coupling strategy should also be applicable to the synthesis of other pyranonaphthoquinone natural products such as kalafungin 4 and nanaomycin 5.