cyclopropylmethyl benzoate | 23293-79-0

• 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: cyclopropylmethyl benzoate
• CAS: 23293-79-0
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: JTHAROHXNNFUDV-UHFFFAOYSA-N

物化性质

• 沸点：
  256.1±9.0 °C(Predicted)
• 密度：
  1.125±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  苯甲醛 在 4-二甲氨基吡啶 、 三氯异氰尿酸 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 121.0h， 生成 cyclopropylmethyl benzoate
  参考文献：
  名称：

  Metal-Free Direct Oxidation of Aldehydes to Esters Using TCCA

  摘要：

  Aromatic and aliphatic aldehydes are simply converted into esters by an efficient oxidative esterification carried out under mild conditions. The aldehydes are converted in situ into their corresponding acyl chlorides, which are then reacted with primary and secondary aliphatic, benzylic, allylic, and propargylic alcohols and phenols. A variety of esters are obtained in high yields.

  DOI：

  10.1021/acs.orglett.5b01579

文献信息

• Synthesis of Esters from Stable and Convenient Sulfoxonium Precursors under Catalyst- and Additive-Free Conditions
  作者：Yang Yuan、Xiao-Feng Wu

  DOI：10.1055/s-0039-1690157

  日期：2019.9

  A convenient and efficient procedure for the construction of esters from stable sulfoxonium ylides and alcohols has been developed. This protocol presents a broad substrate scope and good yields of the desired esters can be isolated. Notably, no catalyst, oxidant, base or any other additive is required.

  已经开发了一种从稳定的锍叶立德和醇中构建酯的方便有效的方法。该协议提供了广泛的底物范围，并且可以分离出所需酯的良好产量。值得注意的是，不需要催化剂、氧化剂、碱或任何其他添加剂。
• Conversion of amides to esters by the nickel-catalysed activation of amide C–N bonds
  作者：Liana Hie、Noah F. Fine Nathel、Tejas K. Shah、Emma L. Baker、Xin Hong、Yun-Fang Yang、Peng Liu、K. N. Houk、Neil K. Garg

  DOI：10.1038/nature14615

  日期：2015.8

  Although enzymes are able to cleave amide bonds in nature, it is difficult to selectively break the carbon–nitrogen bond of an amide using synthetic chemistry; now the activation and cleavage of these bonds using nickel catalysts is used to convert amides to esters. Although enzymes are able to cleave amide bonds in nature, it is difficult to selectively break the carbon–nitrogen bond of an amide using synthetic chemistry. In this paper the authors demonstrate that amide C–N bonds can be activated and cleaved using nickel catalysts. They used this methodology to convert amides to esters, which is a challenging and underdeveloped transformation. Amides are common functional groups that have been studied for more than a century1. They are the key building blocks of proteins and are present in a broad range of other natural and synthetic compounds. Amides are known to be poor electrophiles, which is typically attributed to the resonance stability of the amide bond1,2. Although amides can readily be cleaved by enzymes such as proteases3, it is difficult to selectively break the carbon–nitrogen bond of an amide using synthetic chemistry. Here we demonstrate that amide carbon–nitrogen bonds can be activated and cleaved using nickel catalysts. We use this methodology to convert amides to esters, which is a challenging and underdeveloped transformation. The reaction methodology proceeds under exceptionally mild reaction conditions, and avoids the use of a large excess of an alcohol nucleophile. Density functional theory calculations provide insight into the thermodynamics and catalytic cycle of the amide-to-ester transformation. Our results provide a way to harness amide functional groups as synthetic building blocks and are expected to lead to the further use of amides in the construction of carbon–heteroatom or carbon–carbon bonds using non-precious-metal catalysis.

  尽管酶能够在自然界中断裂酰胺键，但利用合成化学选择性地打破酰胺的碳—氮键却很困难；现在，使用镍催化剂激活和断裂这些键被用于将酰胺转化为酯。本文作者证明，酰胺C—N键可以使用镍催化剂激活和断裂。他们利用这种方法将酰胺转化为酯，这是一种具有挑战性且发展不足的转化。酰胺是一类常见的官能团，一个多世纪以来一直被研究。它们是蛋白质的关键构建模块，存在于广泛的天然和合成化合物中。酰胺被认为是一种差的亲电试剂，这通常归因于酰胺键的共振稳定性。尽管酶如蛋白酶可以轻易地断裂酰胺，但利用合成化学选择性地打破酰胺的碳—氮键却很困难。在这里，我们证明酰胺碳—氮键可以使用镍催化剂激活和断裂。我们利用这种方法将酰胺转化为酯，这是一种具有挑战性且发展不足的转化。反应方法在极其温和的反应条件下进行，并避免了使用大量过量的醇亲核试剂。密度泛函理论计算为酰胺到酯转化的热力学和催化循环提供了见解。我们的结果为利用酰胺官能团作为合成构建块提供了一种方法，并有望进一步在非贵金属催化的碳—杂原子或碳—碳键构建中使用酰胺。
• Efficient and selective palladium-catalyzed direct oxidative esterification of benzylic alcohols under aerobic conditions
  作者：Yongke Hu、Bindong Li

  DOI：10.1016/j.tet.2017.11.025

  日期：2017.12

  A highly efficient palladium-catalyzed approach for the direct oxidative esterification of benzylic alcohols with methanol and long-chain aliphatic alcohols under mild conditions has been achieved. This practical catalyst system exhibits a broad substrate scope and good functional group tolerance. Catalytic amount of Bi(OTf)3 is used as co-catalyst to improve the activity and selectivity of the reactions

  已经实现了在温和条件下用甲醇和长链脂族醇将苄醇直接氧化酯化的高效钯催化方法。这种实用的催化剂体系具有广泛的底物范围和良好的官能团耐受性。催化量的Bi（OTf）3用作助催化剂，以提高反应的活性和选择性。获得了多种酯，产率为43–96％。
• [EN] HETEROAROMATIC DERIVATIVES AND PHARMACEUTICAL APPLICATIONS THEREOF<br/>[FR] DÉRIVÉS HÉTÉROAROMATIQUES ET LEURS APPLICATIONS PHARMACEUTIQUES
  申请人：SUNSHINE LAKE PHARMA CO LTD

  公开号：WO2015161830A1

  公开（公告）日：2015-10-29

  Provided herein are novel heteroaromatic derivatives, or a stereoisomer, a geometric isomer, a tautomer, an N-oxide, a hydrate, a solvate, a prodrug, a pharmaceutically acceptable salt or a prodrug thereof, and pharmaceutical compositions containing such compounds. Also provided herein are uses of such compounds or pharmaceutical compositions thereof in the manufacture of a medicament for treating respiratory diseases, especially chronic obstructive pulmonary disease (COPD).

  本文提供了新颖的杂环芳烃衍生物，或其立体异构体、几何异构体、互变异构体、N-氧化物、水合物、溶剂合物、前药、药用盐或其前药，以及含有这些化合物的药物组合物。本文还提供了这些化合物或药物组合物在制造用于治疗呼吸道疾病，特别是慢性阻塞性肺病（COPD）的药物中的用途。
• Catalytic conversion of ketones to esters <i>via</i> C(O)–C bond cleavage under transition-metal free conditions
  作者：Murugan Subaramanian、Palmurukan M. Ramar、Jagannath Rana、Virendra Kumar Gupta、Ekambaram Balaraman

  DOI：10.1039/d0cc03312j

  日期：——

  The catalytic conversion of ketones to esters via C(O)–C bond cleavage under transition-metal free conditions is reported. This catalytic process proceeds under solvent-free conditions and offers an easy operational procedure, broad substrate scope with excellent selectivity, and reaction scalability.

  据报道，在无过渡金属条件下，酮通过C（O）-C键的裂解催化转化为酯。该催化过程在无溶剂条件下进行，并提供了简便的操作步骤，宽泛的底物范围和出色的选择性以及反应可扩展性。