(-)-menthyl carbamate | 52719-94-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-menthyl carbamate
• 英文别名: (1R,2S,5R)-2-isopropyl-5-methylcyclohexyl carbamate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] carbamate
• CAS: 52719-94-5
• 化学式: C₁₁H₂₁NO₂
• 分子量: 199.293
• InChiKey: SLIAVDGEVKKHIC-KXUCPTDWSA-N

物化性质

• 熔点：
  155-157 °C(Solv: ethanol (64-17-5); water (7732-18-5))
• 沸点：
  305.0±9.0 °C(Predicted)
• 密度：
  0.98±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  52.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (-)-menthyl carbamate 在 氨 、 sodium amide 作用下， 生成
  参考文献：
  名称：

  Stereochemistry of sulfur compounds. VII. Course of substitution at sulfur attached to four different ligands

  摘要：

  DOI：

  10.1021/ja00814a031
• 作为产物：
  描述：

  L-薄荷醇 在 吡啶 、 ammonium hydroxide 作用下， 以 四氢呋喃 、 四氯化碳 、 水 为溶剂， 反应 6.0h， 生成 (-)-menthyl carbamate
  参考文献：
  名称：

  Design and Synthesis of Chiral N-Chloroimidodicarbonates:  Application to Asymmetric Chlorination of Silyl Enol Ethers

  摘要：

  New chiral N-chloroimidodicarbonates, which function as efficient chiral chlorinating agents, were designed and synthesized. Among these, C-2-symmetric (1R,2S,5R)-(-)-menthyl-N-chloroimidodicarbonate 2a provided moderate to good enantioselectivity (up to 40%) for the chlorination of silyl enol ethers to afford alpha-chloroketones only in the presence of a suitable Lewis acid such as Sm(OTf)(3).

  DOI：

  10.1021/jo070614n

文献信息

• Selective Synthesis of Secondary Arylcarbamates via Efficient and Cost Effective Copper-Catalyzed Mono Arylation of Primary Carbamates with Aryl Halides and Arylboronic Acids
  作者：Ali Reza Sardarian、Iman DindarlooInaloo、Milad Zangiabadi

  DOI：10.1007/s10562-017-2277-0

  日期：2018.2

  An efficient, selective and cost-effective procedure has been developed for mono N-arylation of primary alkyl and benzyl carbamates with aryl iodides and bromides by incorporating CuI as an inexpensive and commercially available catalyst. Despite previous reports on C–N coupling reactions, this process does not need expensive ligands and takes advantage of readily available and inexpensive ethylenediamine

  通过引入 CuI 作为廉价且市售的催化剂，已开发出一种高效、选择性和成本效益高的程序，用于伯烷基和苄基氨基甲酸酯与芳基碘化物和溴化物的单 N-芳基化。尽管之前有关于 C-N 偶联反应的报道，但该过程不需要昂贵的配体，并且利用容易获得且价格低廉的乙二胺 (EDA) 作为配体。反应时间相对较短，并且以极好的收率获得了相关的 N-芳基化氨基甲酸酯。有趣的是，用 Cu(OAc)2 代替 CuI 使我们能够使用芳基硼酸作为该反应的偶联伙伴。所有产品均通过 1H- 和 13C-NMR、MS、熔点、IR 和 CHNS 技术进行了充分表征。图形摘要
• Further Development of the Tin-Catalyzed Transcarbamoylation Reaction
  作者：Yoshiyasu Ichikawa、Tomoyuki Hasegawa、Takahiro Minami、Hiroshi Sato、Yukinori Morishita、Rika Ochi、Toshiya Masuda

  DOI：10.1055/s-0040-1708020

  日期：2020.8

  Studies carried out to further develop tin-catalyzed trans­carbamoylation reactions demonstrated that transcarbamoylation of cinnamyl alcohol in the context of allyl cyanate-to-isocyanate rearrangement can be efficiently carried out on a ten-gram scale and that tin-­catalyzed transcarbamoylation is a valuable alternative to the method using trichloroacetyl isocyanate. In addition, methyl carbamate

  为进一步开发锡催化的氨基甲酸酯化反应而进行的研究表明，在烯丙基氰酸酯到异氰酸酯重排的背景下，肉桂醇的氨基甲酸酯化可以有效地在10克规模上进行，并且锡催化的氨基甲酸酯化是一种有价值的替代方法该方法使用三氯乙酰基异氰酸酯。此外，在锡催化的转氨甲酰化反应中发现氨基甲酸甲酯是一种经济的氨基甲酰基供体，该氨基甲酸酯显示出广泛的官能团耐受性，并简化了后处理程序。最后，开发了一种独特的合成方法来制备氨基甲酸酯系萜烯糖结合物。
• An Efficient Synthesis of Carbamates by Tin-Catalyzed Transcarbamoylation Reactions of Primary and Secondary Alcohols
  作者：Yoshiyasu Ichikawa、Yukinori Morishita、Shuhei Kusaba、Naoto Sakiyama、Yasunori Matsuda、Keiji Nakano、Hiyoshizo Kotsuki

  DOI：10.1055/s-0030-1258102

  日期：2010.7

  A new approach to the synthesis of carbamates based on a tin-catalyzed transcarbamoylation process has been developed. Reactions of primary and secondary alcohols with phenyl carbamate in toluene at 90 °C proceed smoothly in the presence of tin-catalyst to generate the corresponding carbamates in good yields. This mild method exhibits a broad functional-group tolerance.

  已经开发了一种基于锡催化氨基甲酰化过程合成氨基甲酸酯的新方法。伯醇和仲醇与氨基甲酸苯酯在 90 °C 的甲苯中在锡催化剂存在下顺利进行反应，以良好的产率生成相应的氨基甲酸酯。这种温和的方法表现出广泛的官能团耐受性。
• Compositions and methods for the treatment of disease associated with Trp-p8 expression
  申请人：Natarajan K. Sateesh

  公开号：US20050054651A1

  公开（公告）日：2005-03-10

  Provided are small-molecule Trp-p8 modulators, including Trp-p8 agonists and Trp-p8 antagonists, and compositions comprising small-molecule Trp-p8 agonists as well as methods for identifying and characterizing novel small-molecule Trp-p8 modulators and methods for decreasing viability and/or inhibiting growth of Trp-p8 expressing cells, methods for activating Trp-p8-mediated cation influx, methods for stimulating apoptosis and/or necrosis, and related methods for the treatment of diseases, including cancers such as lung, breast, colon, and/or prostate cancers as well as other diseases, such as benign prostatic hyperplasia, that are associated with Trp-p8 expression.

  提供了小分子Trp-p8调节剂，包括Trp-p8激动剂和Trp-p8拮抗剂，以及包含小分子Trp-p8激动剂的组合物，以及用于识别和表征新型小分子Trp-p8调节剂的方法，以及用于降低Trp-p8表达细胞的存活能力和/或抑制生长的方法，用于激活Trp-p8介导的阳离子流入的方法，用于刺激凋亡和/或坏死的方法，以及用于治疗疾病的相关方法，包括肺癌、乳腺癌、结肠癌和/或前列腺癌等癌症，以及与Trp-p8表达相关的其他疾病，如良性前列腺增生。
• Metal-Free Stereoselective Synthesis of (<i>E</i>)- and (<i>Z</i>)-N-Monosubstituted β-Aminoacrylates via Condensation Reactions of Carbamates
  作者：Scott R. Pollack、Amélie Dion

  DOI：10.1021/acs.joc.1c01212

  日期：2021.9.3

  acids and pharmaceuticals. Two efficient, stereoselective methods of preparation, via acid- or base-promoted condensation reactions of carbamates, are described. The base-promoted reaction is E-selective, while acid catalysis can, through the choice of solvent, selectively form E or Z. The acid-catalyzed E-selective process proceeds through a crystallization obviating the need for chromatographic purification

  N-单取代的 β-氨基丙烯酸酯是结构单元，已用于制备氨基酸和药物。描述了两种有效的立体选择性制备方法，通过酸或碱促进的氨基甲酸酯缩合反应。碱促进的反应是E选择性的，而酸催化可以通过溶剂的选择选择性地形成E或Z。酸催化的E选择性过程通过结晶进行，无需色谱纯化。