1-[2-(1-hydroxycyclopentylmethyl)allyl]cyclohexan-1-ol | 208466-78-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[2-(1-hydroxycyclopentylmethyl)allyl]cyclohexan-1-ol
• 英文别名: 1-[2-[(1-Hydroxycyclopentyl)methyl]prop-2-enyl]cyclohexan-1-ol
• CAS: 208466-78-8
• 化学式: C₁₅H₂₆O₂
• 分子量: 238.37
• InChiKey: KJOWDFKCNRJPFV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[2-(1-hydroxycyclopentylmethyl)allyl]cyclohexan-1-ol 在 双氧水 、 copper dichloride 、 palladium dichloride 作用下， 以 甲醇 、 水 为溶剂， 反应 8.0h， 生成 (3aR^*,6aS^*)-dispiro[cyclohexane-1,2'-perhydrofuro[2,3-b]furan-5',1''-cyclopentane]
  参考文献：
  名称：

  Wacker型反应直接合成全氢呋喃[2,3- b ]呋喃

  摘要：

  在Wacker型反应条件下，基于分子内缩醛化反应，由容易获得的3-亚甲基-1,5-二醇可以有效地合成取代的全氢呋喃[2,3- b ]呋喃。

  DOI：

  10.1002/adsc.200800339
• 作为产物：
  描述：

  环戊酮 、 1-[2-(2-Methoxy-ethoxymethyl)-allyl]-cyclohexanol 在 萘 、 水 、 lithium 作用下， 以 四氢呋喃 为溶剂， 生成 1-[2-(1-hydroxycyclopentylmethyl)allyl]cyclohexan-1-ol
  参考文献：
  名称：

  2-Chloromethyl-3-(2-methoxyethoxy)propene: Naphthalene-catalysed lithiation and reaction towards electrophiles

  摘要：

  The reaction of the title compound (1) with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of an electrophile [E-1(+)=(BuCHO)-C-t, Et2CO, (CH2)(5)CO, PhCOMe, Me3SiCl] in THF at -78 to -30 degrees C, followed by treatment with a second electrophile [E-2(+)=(BuCHO)-C-t, Me2CO, Et2CO, (CH2)(4)CO, (CH2)(5)CO, (BuCOMe)-C-t, (Bu2CO)-C-t, PhCH=NPh, Me3SiCl, D2O] at -30 degrees C to room temperature leads, after hydrolysis, to the expected compounds 2. For carbonyl derivatives, compounds 2 were successively hydroborated (BH3 . THF) and oxidised [33% H2O2 and then PCC or RuCl2(PPh3)(3)] to give directly the corresponding perhydrofurofurans 4. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)00476-6

文献信息

• New Trimethylenemethane Dianion Synthons: Application to the Preparation of Substituted Perhydrofuro[2,3-b]furans
  作者：Emilio Lorenzo、Francisco Alonso、Miguel Yus

  DOI：10.1016/s0040-4020(00)00060-0

  日期：2000.3

  The reaction of 3-chloro-2-(chloromethyl)prop-1-ene (1) with lithium powder and a catalytic amount of naphthalene in the presence of different electrophiles in THF at −78°C yields products 2. When carbonylic compounds are used as electrophiles the corresponding methylenic diols are obtained, which by tandem hydroboration–oxidation with alkaline hydrogen peroxide and treatment with PCC (for ketone derivatives)

  3-氯-2-（氯甲基）丙-1-烯（1）与锂粉和催化量的萘在不同亲电试剂存在下于-78°C在THF中反应，生成产物2。当将羰基化合物用作亲电子试剂时，会获得相应的亚甲基二醇，这是通过碱式过氧化氢的串联硼氢化-氧化并用PCC（对于酮衍生物）或（Ph 3 P）3 RuCl 2（对于醛衍生物）处理提供的。过氢呋喃呋喃3。使用2-氯甲基-3-（2-甲氧基乙氧基）丙-1-烯（4）作为原料，在上述条件下，选择性的氯/锂交换相对于烯丙基碳-氧键裂解使引入的第一个亲电试剂在-78至-30°C的温度下引入，第二个亲电试剂在-30°C的温度下引入室温下给予产品5。当应用于二醇5时，上述相同的氧化方案会导致不同取代的全氢呋喃呋喃7。
• 2-Chloromethyl-3-(2-methoxyethoxy)propene: Naphthalene-catalysed lithiation and reaction towards electrophiles
  作者：Francisco Alonso、Emilio Lorenzo、Miguel Yus

  DOI：10.1016/s0040-4039(98)00476-6

  日期：1998.5

  The reaction of the title compound (1) with an excess of lithium powder and a catalytic amount of naphthalene (2.5%) in the presence of an electrophile [E-1(+)=(BuCHO)-C-t, Et2CO, (CH2)(5)CO, PhCOMe, Me3SiCl] in THF at -78 to -30 degrees C, followed by treatment with a second electrophile [E-2(+)=(BuCHO)-C-t, Me2CO, Et2CO, (CH2)(4)CO, (CH2)(5)CO, (BuCOMe)-C-t, (Bu2CO)-C-t, PhCH=NPh, Me3SiCl, D2O] at -30 degrees C to room temperature leads, after hydrolysis, to the expected compounds 2. For carbonyl derivatives, compounds 2 were successively hydroborated (BH3 . THF) and oxidised [33% H2O2 and then PCC or RuCl2(PPh3)(3)] to give directly the corresponding perhydrofurofurans 4. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Straightforward Synthesis of Perhydrofuro[2,3-<i>b</i>]furans through a Wacker-Type Reaction
  作者：Francisco Alonso、Daniel Sánchez、Tatiana Soler、Miguel Yus

  DOI：10.1002/adsc.200800339

  日期：2008.9.5

  An efficient synthesis of substituted perhydrofuro[2,3-b]furans has been accomplished from readily accesible 3-methylidene-1,5-diols based on an intramolecular acetalisation under Wacker-type reaction conditions.

  在Wacker型反应条件下，基于分子内缩醛化反应，由容易获得的3-亚甲基-1,5-二醇可以有效地合成取代的全氢呋喃[2,3- b ]呋喃。