camphorsultam | 153153-41-4

• 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: camphorsultam
• 英文别名: (2S)-Bornane-10,2-sultam；10,10-dimethyl-3λ6-thia-4-azatricyclo[5.2.1.01,5]decane 3,3-dioxide
• CAS: 153153-41-4
• 化学式: C₁₀H₁₇NO₂S
• mdl: MFCD00011723
• 分子量: 215.316
• InChiKey: DPJYJNYYDJOJNO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  14
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  54.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  camphorsultam 生成 N-octanoyl-(1S)-(-)-10,2-camphorsultam
  参考文献：
  名称：

  Org. Process Res. Dev. 2003, 7, 168-171

  摘要：

  DOI：
• 作为产物：
  描述：

  camphorsultam, acetylated 在 水 、 三乙胺 、 lithium bromide 作用下， 以 乙腈 为溶剂， 反应 5.0h， 以90%的产率得到camphorsultam
  参考文献：
  名称：

  A mild hydrolysis of esters mediated by lithium salts

  摘要：

  When treated with amine bases such as triethylamine and various lithium salts in wet solvents, esters are efficiently hydrolyzed to the corresponding acids in good yields. Esters incorporating an alpha- or beta-heteroatom with respect to the ester carbonyl group are hydrolyzed rapidly even at room temperature. To further demonstrate the usefulness of this method, one example is provided where hydrolysis of acetylated camphorsultam is mediated by LiBr. (c) 2007 Elsevier Ltd. All riehts reserved.

  DOI：

  10.1016/j.tetlet.2007.02.029
• 作为试剂：
  描述：

  3-(2,3-dihydrobenzofuran-4-yl)-2-propenoyl chloride 、 camphorsultam 在 camphorsultam 作用下， 以92的产率得到
  参考文献：
  名称：

  Benzofuran and dihydrobenzofuran melatonergic agents

  摘要：

  提供了新型苯并呋喃和二氢苯并呋喃衍生物，可用作褪黑素受体激动剂。

  公开号：

  US05856529A1

文献信息

• Di-μ-hydroxy-bis(N,N,N′,N′-tetramethylenediamine)-copper(II) chloride [Cu(OH)·TMEDA]2Cl2: an efficient, practical catalyst for benzylation and allylation of amides
  作者：G. Kumaraswamy、A. Pitchaiah、G. Ramakrishna、D.S. Ramakrishna、K. Sadaiah

  DOI：10.1016/j.tetlet.2006.01.050

  日期：2006.3

  An efficient protocol for the benzylation or allylation of amides using the corresponding benzyl or allyl chlorides as electrophiles under basic conditions with commercially available 5 mol % of [Cu(OH)TMEDA]2Cl2 as catalyst was developed. Under these conditions, unprotected amino acids were benzylated without any racemization.

  开发了一种有效的方案，用于在碱性条件下使用相应的苄基或烯丙基氯作为亲电试剂，使用市售的5 mol％的[Cu（OH）TMEDA] 2 Cl 2作为催化剂，进行酰胺的苄基化或烯丙基化。在这些条件下，未保护的氨基酸被苄基化而没有外消旋作用。
• METHOD FOR THE PRODUCTION OF OPTICALLY ACTIVE ALPHA ALKYL CARBONYL COMPOUNDS
  申请人：Breit Bernhard

  公开号：US20100305352A1

  公开（公告）日：2010-12-02

  A method for the production of optically active α-alkylcarbonyl compounds with retention of the stereo information of the starting compound. The starting compound used here is a carbonyl compound which has, in the α-position, a leaving group which is substituted by an alkyl group with inversion of the configuration. The substitution of the leaving group is effected with the use of an alkylmagnesium Grignard and a zinc (II) salt or a zinc organyl. The method permits the production of optically active α-alkylcarbonyl compounds at very mild temperatures (for example 0° C.) with the use of starting compounds which are easy to prepare and economical and nontoxic catalysts, it also being possible to achieve a very high yield.

  一种生产具有保留起始化合物立体信息的光学活性α-烷基羰基化合物的方法。这里使用的起始化合物是一种具有α-位置上的离去基团的羰基化合物，该离去基团被一个烷基团取代，并且立体构型发生倒转。通过使用烷基镁格氏试剂和锌（II）盐或锌有机基进行离去基团的取代。该方法允许在非常温和的温度条件下（例如0°C）生产光学活性的α-烷基羰基化合物，使用易于制备和经济实惠的起始化合物以及无毒的催化剂，同时也可以获得很高的产率。
• Stereoselective synthesis of the C3–C12 subunit of laulimalide
  作者：Sadagopan Raghavan、Pradip Kumar Samanta

  DOI：10.1016/j.tetlet.2013.12.040

  日期：2014.1

  A stereoselective synthesis of the C3–C12 subunit of the tumor growth inhibitors laulimalide is disclosed. The key steps of the synthesis include asymmetric alkylation using Oppolzer’s protocol and an asymmetric hetero-Diels–Alder reaction using Jacobsen’s catalyst. Substrate controlled diastereoselective Luche reduction followed by Ferrier type reactions are other key steps.

  立体选择性合成肿瘤生长抑制剂laulimalide的C3-C12亚基。合成的关键步骤包括使用Oppolzer方案进行不对称烷基化和使用Jacobsen催化剂进行不对称杂Diels-Alder反应。底物控制的非对映选择性Luche还原，然后进行Ferrier型反应是其他关键步骤。
• Direct Synthesis of CF₂H-Substituted 2-Amidofurans via Copper-Catalyzed Addition of Difluorinated Diazoacetone to Ynamides
  作者：Yongxiang Zheng、Anna Perfetto、Davide Luise、Ilaria Ciofini、Laurence Miesch

  DOI：10.1021/acs.orglett.1c01876

  日期：2021.7.16

  science. Methods for the incorporation of lightly fluorinated groups such as CF2H have been less well developed. Here we report the use of difluorinated diazoacetone as a practical reagent for the direct synthesis of CF2H-substituted 2-amidofurans through addition to ynamides. These newly designed difluorinated amidofurans were elaborated to create new nitrogen-containing frameworks that would be challenging

  含有二氟甲基的分子的重要性是由它们在制药和农业化学科学中的潜在应用驱动的。掺入轻度氟化基团（例如CF 2 H）的方法还没有得到很好的发展。在这里，我们报告了使用二氟化重氮丙酮作为一种实用试剂，通过添加到ynamides直接合成CF 2 H 取代的2-酰氨基呋喃。这些新设计的二氟酰氨基呋喃经过精心设计，以创造新的含氮框架，否则很难获得。
• Processes for the Preparation of Tasimelteon and Intermediates Thereof
  申请人：Apotex Inc.

  公开号：US20170355688A1

  公开（公告）日：2017-12-14

  The present invention provides processes for the preparation of Tasimelteon (1), as well as processes for the preparation of intermediates of Formulas (2), (3) and (4) useful in the preparation of Tasimelteon (1).

  本发明提供了制备Tasimelteon（1）的工艺，以及制备用于制备Tasimelteon（1）的中间体Formula（2）、（3）和（4）的工艺。

表征谱图