1-(Benzyloxy)hexan-2-ol | 136185-70-1

• 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)hexan-2-ol
• 英文别名: 1-Phenylmethoxyhexan-2-ol
• CAS: 136185-70-1
• 化学式: C₁₃H₂₀O₂
• 分子量: 208.301
• InChiKey: KCZWOMWHTZWMGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 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)hexan-2-ol 在 三乙烯二胺 、 正丁基锂 作用下， 以 四氢呋喃 、 乙酸乙酯 为溶剂， 生成 2-phenyl-3-(phenylmethoxymethyl)heptanoic acid
  参考文献：
  名称：

  通过对映体纯的α-烷氧基磺酸盐的SN2反应合成有效的hNK-1受体拮抗剂。

  摘要：

  描述了富含立体化学的hNK-1受体拮抗剂的简明合成。对映体纯的α-烷氧基磺酸盐（正交保护的丁烷三醇）的S（N）2反应是利用salen介导的水解动力学拆分技术制备的，从而突出了该合成反应。采用立体控制的缩醛化连接具有高非对映选择性的两个对映体纯的片段。

  DOI：

  10.1021/ol047925u
• 作为产物：
  描述：

  噁丙环,2-[(苯基甲氧基)甲基]-3-丙基-,(2R,3S)-rel- 在 偶氮二异丁腈 三正丁基氢锡 、 magnesium iodide 作用下， 以 乙醚 、 甲苯 为溶剂， 反应 6.0h， 生成 1-(Benzyloxy)hexan-2-ol
  参考文献：
  名称：

  Regioselective opening of epoxy alcohols: mild chemo- and stereoselective preparation of iodohydrins and 1,2-diols

  摘要：

  Several 2,3-epoxy alcohols have been opened, at -60-degrees-C, with MgI2, leading to the corresponding 3-iodo 1,2-diols with a high level of regio- and chemoselectivity. The iodohydrins can be reduced "in situ", by means of nBu3SnH, to the corresponding 1,2-diols. The chemo-, regio-, and stereocontrol of the reaction makes the method of wide use. Furthermore, epoxy alcohol derivatives (acetyl, benzyl, or TBMS) still maintain a strong preference for C-3 attack of the nucleophile. The experimental data strongly suggest that a metal (Mg) centered chelate is formed throughout the reaction, which gives rise to the regioselective delivery of the iodide ion.

  DOI：

  10.1021/jo00021a045

文献信息

• Erbium(III) Triflate is a Highly Efficient Catalyst for the Synthesis of β-Alkoxy Alcohols, 1,2-Diols and β-Hydroxy Sulfides by Ring Opening of Epoxides
  作者：Monica Nardi、Renato Dalpozzo、Manuela Oliverio、Rosina Paonessa、Antonio Procopio

  DOI：10.1055/s-0029-1216956

  日期：2009.10

  ring-opening reaction of epoxides with erbium(III) triflate are described. Epoxides can be cleaved under neutral conditions with alcohols and thiols in the presence of catalytic amounts of Lewis acid, affording the corresponding β-alkoxy alcohols and β-hydroxy sulfides in high yields. In water, epoxide ring opening occurs to produce the corresponding diols in good yields epoxides - Lewis acids - nucleophilic

  描述了环氧化物与三氟甲磺酸（（III）开环反应中的化学和立体选择性。可以在催化量的路易斯酸存在下，在中性条件下用醇和硫醇裂解环氧化物，以高收率得到相应的β-烷氧基醇和β-羟基硫化物。在水中，发生环氧化物开环以高产率生产相应的二醇 环氧-路易斯酸-亲核加成-开环-绿色化学
• Regioselective Benzylation of Diols and Polyols by Catalytic Amounts of an Organotin Reagent
  作者：Hengfu Xu、Yuchao Lu、Yixuan Zhou、Bo Ren、Yuxin Pei、Hai Dong、Zhichao Pei

  DOI：10.1002/adsc.201301152

  日期：2014.5.26

  An efficient one‐pot method for the selective benzylation of diols and polyols using 0.1 equiv. of organotin reagents and tetrabutylammonium bromide as catalyst has been developed. The diols and polyols containing a cis‐vicinal diol were regioselectively benzylated in 70–94% isolated yields. A catalytic reaction mechanism was also proposed.

  一种高效的一锅法，可使用0.1当量对二醇和多元醇进行选择性苄基化。已开发出有机锡试剂和四丁基溴化铵作为催化剂。含顺式-邻位二醇的二醇和多元醇被区域选择性地苄基化，分离产率为70-94％。还提出了催化反应机理。
• Regioselective opening of epoxy alcohols: mild chemo- and stereoselective preparation of iodohydrins and 1,2-diols
  作者：Carlo Bonini、Giuliana Righi、Giovanni Sotgiu

  DOI：10.1021/jo00021a045

  日期：1991.10

  Several 2,3-epoxy alcohols have been opened, at -60-degrees-C, with MgI2, leading to the corresponding 3-iodo 1,2-diols with a high level of regio- and chemoselectivity. The iodohydrins can be reduced "in situ", by means of nBu3SnH, to the corresponding 1,2-diols. The chemo-, regio-, and stereocontrol of the reaction makes the method of wide use. Furthermore, epoxy alcohol derivatives (acetyl, benzyl, or TBMS) still maintain a strong preference for C-3 attack of the nucleophile. The experimental data strongly suggest that a metal (Mg) centered chelate is formed throughout the reaction, which gives rise to the regioselective delivery of the iodide ion.
• Synthesis of a Potent hNK-1 Receptor Antagonist via an S_N2 Reaction of an Enantiomerically Pure α-Alkoxy Sulfonate
  作者：Todd D. Nelson、Jonathan D. Rosen、Jacqueline H. Smitrovich、Joseph Payack、Bridgette Craig、Louis Matty、Mark A. Huffman、James McNamara

  DOI：10.1021/ol047925u

  日期：2005.1.1

  concise synthesis of a stereochemically rich hNK-1 receptor antagonist is described. The synthesis is highlighted by an S(N)2 reaction of an enantiomerically pure alpha-alkoxy sulfonate (orthogonally protected butane triol), which was prepared by utilizing salen-mediated hydrolytic kinetic resolution technology. A stereocontrolled acetalization was employed to connect two enantiomerically pure fragments

  描述了富含立体化学的hNK-1受体拮抗剂的简明合成。对映体纯的α-烷氧基磺酸盐（正交保护的丁烷三醇）的S（N）2反应是利用salen介导的水解动力学拆分技术制备的，从而突出了该合成反应。采用立体控制的缩醛化连接具有高非对映选择性的两个对映体纯的片段。