1-(cyclohexylmethyl)cyclopropan-1-ol | 1247924-80-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-(cyclohexylmethyl)cyclopropan-1-ol
• CAS: 1247924-80-6
• 化学式: C₁₀H₁₈O
• 分子量: 154.252
• InChiKey: SAOUXADJZZTNQG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 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：

  1-(cyclohexylmethyl)cyclopropan-1-ol 在 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 silver carbonate 作用下， 以 2,2,2-三氟乙醇 为溶剂， 反应 0.25h， 以56%的产率得到1,8-dicyclohexyloctane-2,7-dione
  参考文献：
  名称：

  Rhodium-Catalyzed Room Temperature C–C Activation of Cyclopropanol for One-Step Access to Diverse 1,6-Diketones

  摘要：

  A rhodium-catalyzed room temperature C-C activation of cyclopropanol has been demonstrated for the single-step synthesis of a range of electronically and sterically distinct 1,6-diketones. This reaction proceeds efficiently in shorter reaction time following a highly atom-economical pathway. To illustrate the synthetic potential of 1,6-diketones, aldol and macrocyclization reactions have been successfully demonstrated. Preliminary mechanistic studies revealed the involvement of nonradical pathways.

  DOI：

  10.1021/acs.orglett.0c00967
• 作为产物：
  描述：

  环己基乙酸甲酯 、 乙基溴化镁 在 titanium(IV) isopropylate 作用下， 以 四氢呋喃 为溶剂， 反应 0.67h， 以87%的产率得到1-(cyclohexylmethyl)cyclopropan-1-ol
  参考文献：
  名称：

  Palladium-catalyzed cross-coupling of cyclopropanol-derived ketone homoenolates with aryl bromides

  摘要：

  首次实现了含有β-氢的环丙醇衍生的酮烯醇盐与芳基和杂芳基溴的交叉耦合反应。该反应产率高，适用范围广，并采用了一个简单的催化体系。值得注意的是，所提出的钯烯醇盐不会经历β-氢消除形成相应的α,β-不饱和酮。

  DOI：

  10.1039/c3cc42080a

文献信息

• Palladium-catalyzed cross-coupling of cyclopropanol-derived ketone homoenolates with aryl bromides
  作者：David Rosa、Arturo Orellana

  DOI：10.1039/c3cc42080a

  日期：——

  The cross-coupling reaction of cyclopropanol-derived ketone homoenolates bearing β-hydrogens with aryl and hetaryl bromides has been achieved for the first time. This reaction is high yielding, is broad in scope and uses a simple catalytic system. Notably, the proposed palladium homoenolates do not undergo β-hydride elimination to the corresponding α,β-unsaturated ketones.

  首次实现了含有β-氢的环丙醇衍生的酮烯醇盐与芳基和杂芳基溴的交叉耦合反应。该反应产率高，适用范围广，并采用了一个简单的催化体系。值得注意的是，所提出的钯烯醇盐不会经历β-氢消除形成相应的α,β-不饱和酮。
• Copper(I)-Catalyzed Chemoselective Coupling of Cyclopropanols with Diazoesters: Ring-Opening C−C Bond Formations
  作者：Hang Zhang、Guojiao Wu、Heng Yi、Tong Sun、Bo Wang、Yan Zhang、Guangbin Dong、Jianbo Wang

  DOI：10.1002/anie.201612138

  日期：2017.3.27

  Reported herein is an exceptional chemoselective ring‐opening/C(sp3)−C(sp3) bond formation in the copper(I)‐catalyzed reaction of cyclopropanols with diazo esters. The conventional O−H insertion product is essentially suppressed by judicious choice of reaction conditions. DFT calculations provide insights into the reaction mechanism and the rationale for this unusual chemoselectivity.

  本文报道的是在环丙醇与重氮酯的铜（I）催化反应中特殊的化学选择性开环/ C（sp 3）-C（sp 3）键形成。明智地选择反应条件，基本上可以抑制常规的OH插入产物。DFT计算提供了对这种异常化学选择性的反应机理和原理的见解。
• Uracil-Cu(<scp>i</scp>) catalyst: allylation of cyclopropanols with Morita–Baylis–Hillman alcohols under water-tolerant conditions
  作者：Jingwei Hou、Xiaohong Li、Kaiyu Yan、Lei Zhang、Teck-Peng Loh、Peizhong Xie

  DOI：10.1039/d3sc04890j

  日期：——

  a uracil-copper catalytic system was developed to promote ring-opening allylation of cyclopropanols with allylic alcohols under water-tolerant conditions. A new C–OH bond-breaking model can well resolve the trade-off between the need for acidic activators for C(allyl)–OH bond cleavage and the demand for strong basic conditions for generating homoenolates. Therefore, Morita–Baylis–Hillman alcohols,

  受铜与 DNA 和 RNA 的高亲和力的启发，开发了尿嘧啶-铜催化系统，以促进环丙醇与烯丙醇在耐水条件下的开环烯丙基化。一种新的C-OH键断裂模型可以很好地解决C(烯丙基)-OH键断裂所需的酸性活化剂与生成同烯醇盐所需的强碱性条件之间的权衡。因此，Morita-Baylis-Hillman 醇，而不是它们的预活化版本，可以直接掺入与环丙醇的脱水交叉偶联中，产生水作为唯一的副产物。多种功能化的δ 、 ε-不饱和酮以良好到高的收率和高E-选择性获得。
• Palladium-Catalyzed Cross-Coupling of Benzyl Chlorides with Cyclopropanol-Derived Ketone Homoenolates
  作者：Nisha Nithiy、Arturo Orellana

  DOI：10.1021/ol5027188

  日期：2014.11.21

  The palladium-catalyzed cross-coupling reaction of cyclopropanol-derived ketone homoenolates with benzyl chlorides is reported. This reaction proceeds in high yields with electron-neutral and electron-rich benzyl chlorides; however, yields are low with electron-poor benzyl chlorides. In addition, a range of cyclopropanols can be coupled in good yields. The reaction can be conducted with a low catalyst loading (1% Pd) and on a gram scale without reduction in yield.
• One-Step Synthesis of Quinolines via Palladium-Catalyzed Cross-Coupling of Cyclopropanols with Unprotected ortho-Bromoanilines
  作者：Arturo Orellana、Andrei Nikolaev、Nisha Nithiy

  DOI：10.1055/s-0034-1378613

  日期：——

  The cross-coupling of unprotected ortho-bromoanilines with cyclopropanols yields quinolines in a single operation via an intramolecular condensation and palladium-catalyzed oxidation sequence. The reaction tolerates a variety of cyclopropanols and substituted bromoanilines. Deuterium-labeling experiments provide direct evidence of a second equivalent of bromoaniline serving as the terminal oxidant.