(R,S)-(1l,2u,6u)-2-(Benzyloxy)bicyclo<4.1.0>heptane | 136616-42-7

• 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: (R,S)-(1l,2u,6u)-2-(Benzyloxy)bicyclo<4.1.0>heptane
• 英文别名: (±)-2-(benzyloxy)bicyclo[4.1.0]heptane；(1S,2R,6R)-2-phenylmethoxybicyclo[4.1.0]heptane
• CAS: 136616-42-7
• 化学式: C₁₄H₁₈O
• 分子量: 202.296
• InChiKey: KAAUSUQCVHXKFG-HZSPNIEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  溴甲苯 在 diethylzinc 、 四丁基碘化铵 、 sodium hydride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 12.5h， 生成 (R,S)-(1l,2u,6u)-2-(Benzyloxy)bicyclo<4.1.0>heptane
  参考文献：
  名称：

  A comparison of (chloromethyl)- and (iodomethyl)zinc cyclopropanation reagents

  摘要：

  A study comparing the rate of cyclopropanation of a range of olefins using (chloromethyl)- and (iodomethyl)zinc reagents is described. The (chloromethyl)zinc reagent derived from diethylzinc and chloroiodomethane is generally more reactive than the (iodomethyl)zinc analogue. The use of 1,2-dichloroethane as the solvent for these reactions was shown to be a crucial factor necessary to achieve clean, rapid, high-yielding cyclopropanations. The well-known directing effect of proximal oxygen substituents on the stereochemical outcome of "Simmons-Smith" cyclopropanations was shown to hold for the (chloromethyl)zinc reagent as well. The diethylzinc/chloroiodomethane reagent system in 1,2-dichloroethane should prove to be a valuable alternative to traditional (iodomethyl)zinc-based cyclopropanation reagents.

  DOI：

  10.1021/jo00025a007

文献信息

• Rapid and Safe Continuous‐Flow Simmons‐Smith Cyclopropanation using a Zn/Cu Couple Column
  作者：José Luis Nova‐Fernández、Gustavo Pascual‐Coca、Silvia Cabrera、José Alemán

  DOI：10.1002/adsc.202300665

  日期：2024.2.20

  zinc-copper couple.8 Over the years, several modifications have taken place, substituting either the metal alloy by diethylzinc,9 or the dihalogenated species by a diazo derivative.10 Scheme 1 Open in figure viewerPowerPoint a. Classical Simmons-Smith reaction conditions and its variations through time. b. Semi-flow cyclopropanation using diazo derivatives. c. This work. Although the transformation presents

  过去几十年来，流动化学实验方案的相关性和重要性不断增强，最近发表的有关该领域的越来越多的研究就证明了这一点。1许多众所周知的转变已从间歇式转变为流动式，2因为（微）反应器的使用提供了不同的优势，例如更好的传热和传质或改进对敏感和高活性物质的处理。3对于后一种情况，连续流装置的使用带来了一种非常有用的方式，可以扩大依赖于敏感、反应性或短时活物种的过程。这种化合物的直接在线使用实现了使用批量方法无法实现的新转变，同时减少了危害和废物产生。4 从这个意义上说，使用填充有非均相催化剂和试剂的盒可以更有效地处理危险或反应性物质。由于流量设置通常依赖于内部体积非常小的（微）反应器，因此一次仅混合少量试剂，避免了处理大量反应性、腐蚀性或爆炸性物质的危险。5此外，在过去几年中，填充不同金属的盒已被提出用于多种有机转化，其中完成了敏感有机金属物质的原位生产。6 另一方面，Simmons-Smith 反应是从
• SULFONAMIDES DERIVED FROM TRICYCLYL-2-AMINOCYCLOALKANOLS AS ANTICANCER AGENTS
  申请人：ICAHN SCHOOL OF MEDICINE AT MOUNT SINAI

  公开号：US20170015625A1

  公开（公告）日：2017-01-19

  A genus of arylsulfonamide derivatives of aminocycloalkanols is disclosed. The compounds are of the following genus: The compounds induce FOXO1 transcription factor translocation to the nucleus by modulating PP2A and, as a consequence, exhibit anti-proliferative effects. They are useful in the treatment of a variety of disorders, including as a monotherapy in cancer treatment, or used in combination with other drugs to restore sensitivity to chemotherapy where resistance has developed.
• US9937186B2
  申请人：——

  公开号：US9937186B2

  公开（公告）日：2018-04-10