cis-1,2-cyclopropanedicarboxylic acid anhydride | 5617-74-3

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: cis-1,2-cyclopropanedicarboxylic acid anhydride
• 英文别名: 3-oxabicyclo[3.1.0]hexane-2,4-dione；(1R,5S)-3-oxabicyclo[3.1.0]hexane-2,4-dione；(1S,5R)-3-Oxabicyclo[3.1.0]hexane-2,4-dione
• CAS: 5617-74-3
• 化学式: C₅H₄O₃
• 分子量: 112.085
• InChiKey: ZRMYHUFDVLRYPN-WSOKHJQSSA-N

物化性质

• 熔点：
  59-61 °C(lit.)
• 沸点：
  100-102 °C5 mm Hg(lit.)
• 密度：
  1.50
• 溶解度：
  溶于甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  8
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  43.4
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 海关编码：
  2917209090
• 安全说明：
  S26,S37/39
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  cis-1,2-cyclopropanedicarboxylic acid anhydride 在 水 作用下， 反应 1.0h， 以95%的产率得到cis-1,2-cyclopropanedicarboxylic acid
  参考文献：
  名称：

  Design and Synthesis of Novel Dimeric Morphinan Ligands for κ and μ Opioid Receptors

  摘要：

  A novel series of morphinans were synthesized, and their binding affinity at and functional selectivity for mu, delta, and kappa opioid receptors were evaluated. These dimeric ligands can be viewed as dimeric morphinans, which were formed by coupling two identical morphinan pharmacophores (cyclorphan (1) or MCL 101 (2)) with varying connecting spacers. Ligands 6 and 7 with alkyl spacers on the nitrogen position and ligands 8 and 9 in which the two morphinan pharmacophores were coupled by ether moieties at the 3-hydroxyl positions showed significant decrease in affinity at all three opioid receptors. An improvement in the affinity was achieved by introducing an ester moiety as the spacer in the dimeric morphinans. It was observed that the affinity of these ligands was sensitive to the character and length of the spacer. Compound 13 (MCL-139) with a 4-carbon ester spacer, compound 17 (MCL-144) containing a 10-carbon spacer, and compound 19 (MCL-145) with the conformationally constrained fumaryl spacer were the most potent ligands in this series, displaying excellent affinities at mu and kappa receptors (K-i = 0.09-0.2 nM at mu and K-i = 0.078-0.049 nM at kappa), which were comparable to the parent compound 2. Ligand 12, a compound containing only one morphinan pharmacophore and a long-chain ester group, had affinity at both mu and kappa receptors almost identical to that of the parent ligand 2. In the [S-35]GTPgammaS binding assay, ligands 13, 17, and 19 and their parent morphinans 1 and 2 stimulated [S-35]GTPgammaS binding mediated by the mu and kappa receptors. Compounds 13 and 17 were full kappa agonists and partialy mu agonists, while compound 19 was a partial agonist at both gamma and kappa receptors. These novel ligands, as well as their interesting pharmacological properties, will serve as the basis for our continuing investigation of the dimeric ligands as potential probes for the pharmacotherapy of cocaine abuse and may also open new avenues for the characterization of opioid receptors.

  DOI：

  10.1021/jm030139v
• 作为产物：
  描述：

  反式 环丙烷-1,2-二羧酸 在 三氟乙酸酐 作用下， 生成 cis-1,2-cyclopropanedicarboxylic acid anhydride
  参考文献：
  名称：

  2.1.1.5 The spatial distribution of earthquake foci

  摘要：

  该文档是《Landolt-Börnstein - V组地球物理学》第2卷《固体地球、月球和行星的地球物理学》子卷A的一部分。

  DOI：

  10.1007/10201917_18

文献信息

• Aerobic Lactonization of Diols by Biomimetic Oxidation
  作者：Yoshinori Endo、Jan-E. Bäckvall

  DOI：10.1002/chem.201102168

  日期：2011.11.4

  Coming up for air: Highly efficient aerobic lactonization can be carried out by a biomimetic oxidation system based on coupled redox catalysts (ruthenium catalyst and electron transfer mediators). This system leads to a low‐energy electron transfer from diol to molecular oxygen. Various diols were aerobically oxidized to the corresponding five‐ to nine‐membered lactones in good to high yields under

  空气进入：高效的好氧内酯化反应可以通过基于偶合氧化还原催化剂（钌催化剂和电子传递介体）的仿生氧化系统进行。该系统导致低能电子从二醇转移到分子氧。在温和的反应条件下，各种二醇被好氧氧化成相应的五元至九元内酯（见方案）。
• Highly Enantioselective Hydrogenative Desymmetrization of Bicyclic Imides Leading to Multiply Functionalized Chiral Cyclic Compounds
  作者：Masato Ito、Chika Kobayashi、Akio Himizu、Takao Ikariya

  DOI：10.1021/ja105048c

  日期：2010.8.25

  Highly enantioselective hydrogenative desymmetrization of bicyclic imides has been developed with chiral Cp*Ru(PN) catalysts. The present hydrogenation directly provides stereochemically well-defined cyclic compounds with excellent enantiomeric exessses, which might otherwise require a detour to reach.

  使用手性 Cp*Ru(PN) 催化剂开发了双环酰亚胺的高度对映选择性氢化去对称化。本氢化直接提供立体化学明确定义的环状化合物，具有优异的对映异构体，否则可能需要绕道而行。
• Practical and Highly Enantioselective Ring Opening of Cyclic <i>Meso</i>-Anhydrides Mediated by Cinchona Alkaloids
  作者：Carsten Bolm、Ingo Schiffers、Christian L. Dinter、Arne Gerlach

  DOI：10.1021/jo000638t

  日期：2000.10.1

  The cinchona alkaloid-mediated opening of prochiral cyclic anhydrides in the presence of methanol leading to optically active hemiesters is described. Very structurally diverse anhydrides are converted into their corresponding methyl monoesters, and either enantiomer can be obtained with up to 99% ee by using quinine or quinidine as directing additive. After the reaction, the alkaloids can be recovered

  描述了在甲醇存在下金鸡纳生物碱介导的前手性环酐的打开，导致旋光性半酯。结构非常不同的酸酐被转化为其相应的甲基单酯，通过使用奎宁或奎尼丁作为直接添加剂，可以以高达99％ee的形式获得任何一种对映体。反应后，几乎可以定量回收生物碱并重新使用，而不会损失对映选择性。另外，提出了一种催化方案，该方案允许在容易获得的五甲基哌啶（哌啶）存在下亚化学计量使用奎尼丁。
• Photodecarbonylation of chiral cyclobutanones
  作者：Jailall Ramnauth、Edward Lee-Ruff

  DOI：10.1139/v97-060

  日期：1997.5.1

  Triplet photosensitized irradiation of 2(S),3(R)-bis[(benzoyloxy)methyl]cyclobutanone gave optically pure (−)E-1(S),2(S)-bis(benzoyloxymethyl)cyclopropane as a major product in the nonpolar fraction along with its stereoisomer and cycloelimination products. The absolute stereochemistry of the chiral cyclopropane was established by independent synthesis and X-ray crystal structure determination of a synthetic precursor. The distribution of decarbonylation and cycloelimination products was inversely dependent on the concentration of the substrate. Irradiation of the same ketone in tetrahydrofuran or benzene gave mostly cycloelimination products. Addition of Michler's ketone increased the ratio of photodecarbonylation, suggesting a triplet state pathway for this process. This was corroborated by the addition of dicyanoethylene, which showed significant quenching of photodecarbonylation. Irradiation of 2(S)-[(benzoyloxy)methyl]cyclobutane in acetone gave the corresponding cyclopropane as the principal product. Keywords: photodecarbonylation, chiral cyclopropanes, cyclobutanones, triplet sensitization.

  三重光敏辐照2(S),3(R)-双[(苯甲酰氧基)甲基]环丁酮，在非极性分馏物中主要生成光学纯的(−)E-1(S),2(S)-双(苯甲酰氧基甲基)环丙烷，同时还有其立体异构体和环消除产物。手性环丙烷的绝对立体化学通过独立合成和合成前体的X射线晶体结构测定来确定。脱羰基化和环消除产物的分布与底物浓度呈反比关系。在四氢呋喃或苯中辐照相同的酮主要生成环消除产物。添加米克勒酮增加了光解脱羰作用的比例，表明了这一过程的三重态途径。通过添加二氰乙烯来证实这一点，显示了光解脱羰作用的显著猝灭。在丙酮中辐照2(S)-[(苯甲酰氧基)甲基]环丁烷产生相应的环丙烷作为主要产物。关键词：光解脱羰作用，手性环丙烷，环丁酮，三重敏化。
• Pyrrolopyrazine Kinase Inhibitors
  申请人：Hendricks Robert Than

  公开号：US20110230462A1

  公开（公告）日：2011-09-22

  The present invention relates to the use of novel pyrrolopyrazine derivatives of Formula I, wherein the variables n, p, q, Q, X, X′ and Y are defined as described herein, which inhibit JAK and SYK and are useful for the treatment of auto-immune and inflammatory diseases.

  本发明涉及使用新型吡咯吡嗪衍生物的公式I，其中变量n、p、q、Q、X、X'和Y如本文所述定义，这些衍生物抑制JAK和SYK，并且适用于治疗自身免疫和炎症性疾病。