trans-ethyl 2-(naphthalen-2-yl)cyclopropane-1-carboxylate | 93433-96-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: trans-ethyl 2-(naphthalen-2-yl)cyclopropane-1-carboxylate
• 英文别名: trans-ethyl 2-(2-naphthalenyl)cyclopropanecarboxylate；ethyl 2-(naphthalen-2-yl)cyclopropane-1-carboxylate；trans-2--cyclopropan-carbonsaeure-(1)-aethylester；trans-ethyl 2-naphthylcyclopropanecarboxylate；trans-(+/-)-2-naphthalen-2-yl-cyclopropanecarboxylic acid ethyl ester；ethyl (1S,2S)-2-naphthalen-2-ylcyclopropane-1-carboxylate
• CAS: 93433-96-6
• 化学式: C₁₆H₁₆O₂
• 分子量: 240.302
• InChiKey: OASMPQRUPGSFOB-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-ethyl 2-(naphthalen-2-yl)cyclopropane-1-carboxylate 在 甲醇 、 potassium hydroxide 作用下， 生成 2-(naphthalen-2-yl)cyclopropanecarboxylic acid
  参考文献：
  名称：

  Selective 5-Hydroxytryptamine 2C Receptor Agonists Derived from the Lead Compound Tranylcypromine: Identification of Drugs with Antidepressant-Like Action

  摘要：

  We report here the design, synthesis, and pharmacological properties of a series of compounds related to tranylcypromine (9), which itself was discovered as a lead compound in a high-throughput screening campaign. Starting from 9, which shows modest activity as a 5-HT2C agonist, a series of 1-aminomethyl-2-phenylcyclopropanes was investigated as 5-HT2C agonists through iterative structural modifications. Key pharmacophore feature of this new class of ligands is a 2-aminomethyl-trans-cyclopropyl side chain attached to a substituted benzene ring. Among the tested compounds, several were potent and efficacious 5-HT2C receptor agonists with selectivity over both 5-HT2A and 5-HT2B receptors in functional assays. The most promising compound is 37, with 120- and 14-fold selectivity over 5-HT2A and 5-HT2B, respectively (EC50 = 585, 65, and 4.8 nM at the 2A, 2B, and 2C subtypes, respectively). In animal studies, compound 37 (10-60 mg/kg) decreased immobility time in the mouse forced swim test.

  DOI：

  10.1021/jm801354e
• 作为产物：
  描述：

  4-(2-萘)-4-氧丁酸 在 potassium tert-butylate 作用下， 以 叔丁醇 、 苯 为溶剂， 生成 trans-ethyl 2-(naphthalen-2-yl)cyclopropane-1-carboxylate
  参考文献：
  名称：

  Kaiser,C. et al., Journal of medicinal and pharmaceutical chemistry, 1962, vol. 5, p. 1243 - 1265

  摘要：

  DOI：

文献信息

• A transition-metal-free & diazo-free styrene cyclopropanation
  作者：Ana G. Herraiz、Marcos G. Suero

  DOI：10.1039/c9sc02749a

  日期：——

  An operationally simple and broadly applicable novel cyclopropanation of styrenes using gem-diiodomethyl carbonyl reagents has been developed. Visible-light triggered the photoinduced generation of iodomethyl carbonyl radicals, able to cyclopropanate a wide array of styrenes with excellent chemoselectivity and functional group tolerance. To highlight the utility of our photocyclopropanation, we demonstrated

  已经开发出一种操作简单且广泛适用的新型苯乙烯环丙烷化反应，该反应使用偕二碘甲基羰基试剂。可见光触发光诱导产生碘甲基羰基自由基，能够使多种苯乙烯环丙烷化，具有优异的化学选择性和官能团耐受性。为了突出我们的光环丙烷化的实用性，我们展示了生物分子衍生物的后期功能化。
• Stereoselective Cyclopropanation of Electron-Deficient Olefins with a Cofactor Redesigned Carbene Transferase Featuring Radical Reactivity
  作者：Daniela M. Carminati、Rudi Fasan

  DOI：10.1021/acscatal.9b02272

  日期：2019.10.4

  catalysts for asymmetric olefin cyclopropanation reactions via carbene-transfer chemistry. Despite this progress, the transformation of electron-poor alkenes has proven to be very challenging using these systems. Here, we describe the design of a myoglobin-based carbene transferase incorporating a non-native iron-porphyrin cofactor and axial ligand, as an efficient catalyst for the asymmetric cyclopropanation

  工程化的肌球蛋白和其他血蛋白最近作为通过卡宾转移化学进行不对称烯烃环丙烷化反应的有前途的催化剂而出现。尽管取得了这些进展，但是使用这些系统已证明贫电子烯烃的转化非常具有挑战性。在这里，我们描述了一种基于肌红蛋白的卡宾转移酶的设计，该酶结合了非天然的铁卟啉辅因子和轴向配体，作为缺电子烯烃的不对称环丙烷化的有效催化剂。使用这种金属酶，可以高效，高非对映和对映选择性（高达> 99％的de和ee）对大量富电子和缺电子的烯烃进行环丙烷化反应。机理研究表明，由于在金属中心周围重新构型的配位环境，该卡宾转移酶的反应范围扩大取决于对金属卡宾自由基反应性的获得。该系统的基于自由基的反应性不同于肌红蛋白和大多数已知的有机金属卡宾转移催化剂的亲电反应性。这项工作展示了辅因子重新设计对调节和扩大生物反应中金属蛋白反应性的价值，并且为缺电子烯烃的不对称环丙烷化提供了生物催化解决方案。预期该生物催化剂表现出的金属碳自
• Metal‐Free Ring Opening Cyclization of Cyclopropane Carbaldehydes and <i>N</i> ‐Benzyl Anilines: An Eco‐Friendly Access to Functionalized Benzo[ <i>b</i> ]azepine Derivatives
  作者：Raghunath Dey、Prabal Banerjee

  DOI：10.1002/adsc.201801714

  日期：2019.6.18

  Herein, we report a p‐toluenesulfonic acid (PTSA) initiated mild and user‐friendly ring opening/domino ring opening cyclization reaction (depends on substituent present in N‐benzyl aniline) of cyclopropane carbaldehyde and N‐benzyl aniline towards the formation of substituted 4‐amino butanal/2,3‐dihydro‐1H‐benzo[b]azepine. The product dihydro‐1H‐benzo[b]azepine was also converted into the corresponding

  在此，我们报道了对丙烷磺酸和环丙烷苯甲醛与N-苄基苯胺的对甲苯磺酸（PTSA）引发的温和且用户友好的开环/多米诺环开环反应（取决于N-苄基苯胺中存在的取代基） 4-氨基丁醛/ 2,3-二氢-1 H-苯并[ b ]氮杂。产物二氢-1 H-苯并[ b ]氮杂也被转化为相应的四氢-1 H-苯并[ b ]氮杂。
• Regioselective Brønsted Acid-Catalyzed Annulation of Cyclopropane Aldehydes with <i>N</i>′-Aryl Anthranil Hydrazides: Domino Construction of Tetrahydropyrrolo[1,2-<i>a</i>]quinazolin-5(1<i>H</i>)ones
  作者：Priyanka Singh、Navpreet Kaur、Prabal Banerjee

  DOI：10.1021/acs.joc.9b03170

  日期：2020.3.6

  synthesis of tetrahydropyrrolo[1,2-a]quinazolin-5(1H)one derivatives was achieved by reacting cyclopropane aldehydes with N'-aryl anthranil hydrazides in the presence of p-toluene sulfonic acid (PTSA). The transformation involves domino imine formation and intramolecular cyclization to form 2-arylcyclopropyl-2,3-dihydroquinolin-4(1H)-one, followed by nucleophilic ring opening of the cyclopropyl ring to form

  在对甲苯磺酸（PTSA）存在下，通过使环丙烷醛与N'-芳基邻氨基苯甲酰肼反应，可以实现对四氢吡咯并[1,2-a]喹唑啉-5（1H）酮衍生物的高度区域选择性合成。该转化涉及多米诺亚胺的形成和分子内环化以形成2-芳基环丙基-2,3-二氢喹啉-4（1H）-一个，然后环丙基环的亲核开环形成所需的四氢吡咯并[1,2-a]喹唑啉- 5（1H）1具有良好的收率，并且具有完全的区域选择性。该方案可耐受多种官能团，因此为吡咯并喹唑啉酮的合成提供了一种简单而高效的方法。
• Accessing Dihydro-1,2-oxazine via Cloke–Wilson-Type Annulation of Cyclopropyl Carbonyls: Application toward the Diastereoselective Synthesis of Pyrrolo[1,2-<i>b</i>][1,2]oxazine
  作者：Pankaj Kumar、Rakesh Kumar、Prabal Banerjee

  DOI：10.1021/acs.joc.0c00531

  日期：2020.5.15

  A convenient additive-free synthesis of dihydro-4H-1,2-oxazines via a Cloke-Wilson-type ring expansion of the aryl-substituted cyclopropane carbaldehydes with the hydroxylamine salt is introduced. Comparatively less active cyclopropyl ketones also follow a similar protocol if supplemented by catalytic p-toluene sulfonic acid monohydrate. The transformation is performed in an open-to-air flask as it

  通过芳基取代的环丙烷甲醛与羟胺盐的Cloke-Wilson型扩环，方便地合成了二氢-4H-1,2-恶嗪。如果由催化对甲苯磺酸一水合物补充，则活性相对较低的环丙基酮也遵循类似的方案。由于它对空气/水分的敏感性可以忽略不计，因此在露天烧瓶中进行转化。当二氢-4H-1,2-恶嗪与环丙烷二酯进行环加成反应时，可以很容易地配制出有价值的六氢-2H-吡咯并[1,2-b] [1,2]恶嗪衍生物。这种两步策略的级联一锅法变体可提供最终产品相当的总产量。