trans-1,2-bis(bromomethyl)cyclopropane

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 有机溴化物
• 英文名称: trans-1,2-bis(bromomethyl)cyclopropane
• 英文别名: (1R,2R)-1,2-bis(bromomethyl)cyclopropane
• 化学式: C₅H₈Br₂
• 分子量: 227.927
• InChiKey: BYTFOVGHZSNHNT-WHFBIAKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  trans-1,2-bis(bromomethyl)cyclopropane 在 sodium hydroxide 、 正丁基锂 、 草酰氯 、 2,4,6-三异丙基苯磺酰叠氮化物 、 水 、 双(三甲基硅烷基)氨基钾 、 N,N-二甲基甲酰胺 作用下， 以 乙醇 、 二氯甲烷 、 水 为溶剂， 反应 27.2h， 生成 (1S,2S)-1,2-bis[(1S)-azido-2-oxo-2((4S)-benzyl-2-oxo-3-oxazolidinyl)ethyl]cyclopropane
  参考文献：
  名称：

  立体选择性合成环丙烷-1,2-双（甘氨酸）衍生物

  摘要：

  已经在立体选择性合成中制备了作为环丙烷的反式衍生物的构象受限的双（甘氨酸）。（S）-4-苄基-2-恶唑烷酮用作手性助剂，叠氮化三甲苯是胺氮的亲电子源。创建了四个立体成因中心。相关的顺式-环丙烷衍生物发生闭环，形成双环[3.1.0] hex-3-one衍生物。后者和（1S，2S）-1,2-双{（1S）-叠氮基-2-氧代-2 [（4S）-苄基-2-氧代-3-恶唑烷基]-乙基}的X射线数据给出了环丙烷0615 0221。

  DOI：

  10.1016/s0040-4020(97)00657-1
• 作为产物：
  描述：

  反-1,2-环丙烷二羧酸二乙酯 在 lithium aluminium tetrahydride 、 溴 、 三苯基膦 作用下， 以 甲基叔丁基醚 、 乙腈 为溶剂， 反应 6.0h， 生成 trans-1,2-bis(bromomethyl)cyclopropane
  参考文献：
  名称：

  高区域选择性钴催化内炔烃的硼氢化

  摘要：

  利用新开发的环丙烷基二膦配体修饰的钴催化剂，实现了不对称内炔烃的高选择性硼氢化反应，该反应具有独特的区域选择性、广泛的底物范围和良好的官能团相容性。目前的协议能够合成新的烯基硼酸盐，并提高了生物活性化合物的合成效率。

  DOI：

  10.1002/anie.202208473

文献信息

• Synthesis and Application of Chiral Cyclopropane-Based Ligands in Palladium-Catalyzed Allylic Alkylation
  作者：Gary A. Molander、Jason P. Burke、Patrick J. Carroll

  DOI：10.1021/jo048782s

  日期：2004.11.1

  A series of chiral, cyclopropane-based phosphorus/sulfur ligands have been synthesized and evaluated in the palladium-catalyzed allylic alkylation of 1,3-diphenylpropenyl acetate with dimethyl malonate. Variation of the ligand substituents at phosphorus, sulfur, and the carbon backbone revealed 24d to have the optimal configuration for this reaction, giving the product in high yield and with good enantioselectivity

  已经合成了一系列手性的，基于环丙烷的磷/硫配体，并在钯催化的1,3-二苯基丙烯基乙酸甲酯与丙二酸二甲酯的钯催化的烯丙基烷基化反应中进行了评估。磷，硫和碳主链上的配体取代基的变化揭示了24d具有该反应的最佳构型，从而以高收率和良好的对映选择性（93％）提供了产物。使用X射线晶体学数据，溶液相NMR研究和产物的绝对立体化学，在现有模型的背景下讨论了观察到的对映选择性的模型。还在钯催化的分子间Heck反应和铑催化的脱氢氨基酸氢化中评估了选定的配体。
• Influence of the Linker in Bispyridium Compounds on the Inhibition of Human Choline Kinase
  作者：Ana Conejo-García、Mónica Báñez-Coronel、Rosario M. Sánchez-Martín、Agustín Rodríguez-González、Angeles Ramos、Ana Ramírez de Molina、Antonio Espinosa、Miguel Angel Gallo、Joaquín M. Campos、Juan Carlos Lacal

  DOI：10.1021/jm0496537

  日期：2004.10.1

  Studies have been aimed to establish the structure-activity relationship that define choline kinase (ChoK) inhibitory potency and antiproliferative activity of a set of 25 bispyridinium compounds with electron-releasing groups at position 4. Here we report that, according to their inhibitory activities against human ChoK, the enzymatic inhibitory potency is closely related to the size of the linker, the 3,3'-biphenyl moiety being the most suitable. The N-methylanilino and its derivatives, 4-chloro-N-methylanilino and 3,5-dichloro-N-methylanilino, render higher ChoK inhibitory and antiproliferative activities against the HT-29 human colon cancer cell line.
• Cyclopropane-Containing Polyamine Analogues Are Efficient Growth Inhibitors of a Human Prostate Tumor Xenograft in Nude Mice
  作者：Benjamin Frydman、Andrei V. Blokhin、Sara Brummel、George Wilding、Yulia Maxuitenko、Aparajita Sarkar、Subhra Bhattacharya、Dawn Church、Venodhar K. Reddy、John A. Kink、Laurence J. Marton、Aldonia Valasinas、Hirak S. Basu

  DOI：10.1021/jm030175u

  日期：2003.10.1

  Polyamine analogues 7, 10, 18, 27, and 32 containing cyclopropane rings were obtained by chemical synthesis. Their antineoplastic activities were assessed against the cultured human prostate tumor cell lines DU-145, DuPro, and PC-3. Decamines 32 and 27 exhibited variable levels of cytotoxicity against all three cell lines, while 7, 10, and 18 were efficacious against DU-145 and DuPro. Maximum tolerated doses (MTD) for all five compounds in a NCr-nu mouse model were determined at dosing schedules of q1d x 5 (ip) in two cycles with a break of 10 days between cycles. Their antitumor efficacies were then tested against DU-145 tumor xenografts in mice treated with all five agents at their respective MTDs. In addition, the efficacies of 7 and 10 against the same tumor xenograft were assessed at doses below their respective MTDs. In all experiments, administration began two weeks after tumor implantation. All compounds efficiently inhibited tumor growth for up to 50 days postimplantation, with negligible animal body weight loss. Tetramine 10 and hexamine 18 were the most efficient among the five analogues in arresting tumor growth. Tetramine 10 containing two cyclopropane rings had the lowest systemic toxicity as reflected in animal body weight loss. It was further assessed at a weekly administration regimen of (q1w x 4) in two cycles with a four-week break between the cycles. At this dosing schedule, 10 again efficiently arrested tumor growth with negligible effect on animal body weight. Tetramine 10 also arrested the growth of large tumors (ca. 2000 mm(3)) treated 66 days postimplantation. Studies on the metabolism of 10 showed that it accumulates in tumor within 6 h after the end of administration and reached a maximum level 72 h after cessation of dosing. Intracellular concentrations of 10 in liver and kidney were much smaller when compared to those in the tumor when measured 72 h after cessation of dosing. In liver and kidney, the deethyl metabolites of 10 accumulated over a 96 h period after cessation of dosing.
• Stereoselective synthesis of cyclopropane-1,2-bis(glycine) derivatives
  作者：Siren Neset、Håkon Hope、Kjell Undheim

  DOI：10.1016/s0040-4020(97)00657-1

  日期：1997.7

  constrained bis(glycines) as trans derivatives of cyclopropane have been prepared in stereoselective syntheses. (S)-4-Benzyl-2-oxazolidinone was used as a chiral auxiliary, trisyl azide was the electrophilic source of amine nitrogen. Four stereogenic centers were created. A related cis-cyclopropane derivative suffered ring closure with formation of a bicyclo[3.1.0]hex-3-one derivative. X-ray data for

  已经在立体选择性合成中制备了作为环丙烷的反式衍生物的构象受限的双（甘氨酸）。（S）-4-苄基-2-恶唑烷酮用作手性助剂，叠氮化三甲苯是胺氮的亲电子源。创建了四个立体成因中心。相关的顺式-环丙烷衍生物发生闭环，形成双环[3.1.0] hex-3-one衍生物。后者和（1S，2S）-1,2-双（1S）-叠氮基-2-氧代-2 [（4S）-苄基-2-氧代-3-恶唑烷基]-乙基}的X射线数据给出了环丙烷0615 0221。
• Highly Regioselective Cobalt‐Catalyzed Hydroboration of Internal Alkynes
  作者：Yan‐Dong Zhang、Xiao‐Yu Li、Qian‐Kun Mo、Wen‐Bin Shi、Jia‐Bao Zhao、Shou‐Fei Zhu

  DOI：10.1002/anie.202208473

  日期：2022.9.5

  A highly selective hydroboration of unsymmetrical internal alkynes featuring unique regioselectivity, broad substrate scope and good functional group compatibility was realized by using cobalt catalysts modified with newly developed cyclopropane-based diphosphine ligands. The current protocol enabled the synthesis of novel alkenyl borates and improved the synthetic efficiency of bioactive compounds

  利用新开发的环丙烷基二膦配体修饰的钴催化剂，实现了不对称内炔烃的高选择性硼氢化反应，该反应具有独特的区域选择性、广泛的底物范围和良好的官能团相容性。目前的协议能够合成新的烯基硼酸盐，并提高了生物活性化合物的合成效率。