1-benzyloxy-2,5-dihydro-phosphole 1-oxide | 163929-68-8

• 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: 1-benzyloxy-2,5-dihydro-phosphole 1-oxide
• 英文别名: 1-benzyloxy-2,5-dihydrophosphole-1-oxide；1-(benzyloxy)phosphol-3-ene 1-oxide；1-benzyloxy-3-phospholene 1-oxide；1-(phenylmethoxy)phospholen-1-one；1-(Benzyloxy)-2,5-dihydrophosphole 1-oxide；1-phenylmethoxy-2,5-dihydro-1λ5-phosphole 1-oxide
• CAS: 163929-68-8
• 化学式: C₁₁H₁₃O₂P
• 分子量: 208.197
• InChiKey: YWGOJNZTPURZFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-benzyloxy-2,5-dihydro-phosphole 1-oxide 在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 以72%的产率得到1-benzyloxy-3,4-epoxy-2,3,4,5-tetrahydrophosphole-1-oxide
  参考文献：
  名称：

  半抗原的合成及旨在催化碳负离子环化反应的催化抗体的性质

  摘要：

  在狄克曼环化和相关反应的背景下，介绍了半抗原的设计，以产生具有催化碳负离子环化反应潜力的抗体。描述了含有砜的五元环半抗原的合成，以代表与四面体中间体相关的过渡态，以及一个氨基基团，以促进一般碱基的形成。报告了部分纯化抗体的结果，表明目标反应可以被抗体催化

  DOI：

  10.1016/0040-4020(95)00500-8
• 作为产物：
  描述：

  bis-cinnamyl-phosphinic acid benzyl ester 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 以53%的产率得到1-benzyloxy-2,5-dihydro-phosphole 1-oxide
  参考文献：
  名称：

  通过钯催化的 H-次膦酸与烯丙醇烯丙基化生成烯丙基次膦酸盐。

  摘要：

  描述了 H-次膦酸的新型催化烯丙基化。使用 Pd/xantphos (2 mol %)，H-次膦酸直接与烯丙醇反应生成 P-烯丙基化的二取代次膦酸。

  DOI：

  10.1021/ol8000415

文献信息

• Asparagine deaminase catalytic antibodies
  申请人：Mulkerrin G. Michael

  公开号：US20050084488A1

  公开（公告）日：2005-04-21

  Transition state analogs are described which may be used to elicit antibodies that catalyze the conversion of asparagine to aspartic acid. Synthetic schemes are disclosed for making the transition state analogs which can than be attached to a carrier molecule to form an immunoconjugate. Immunoconjugates can be administered to an animal for the purpose of raising antibodies. Antibodies can in turn be used in pharmaceutical compositions which can be given to patients as part of a method of treating various conditions, particularly cancer.

  描述了可以用来诱导催化天冬氨酸转化为天冬酸的抗体的过渡态类似物。公开了用于制备过渡态类似物的合成方案，然后可以将其连接到载体分子上形成免疫结合物。可以将免疫结合物注射给动物，以提高抗体水平。抗体反过来可以用于制备药物组合物，可以作为治疗各种疾病，特别是癌症的方法的一部分给患者使用。
• Design and Synthesis of Haptens for the Catalytic Antibody-Promoted Dynamic Kinetic Resolution of Oxazolin-5-ones
  作者：Anne Briot、Murielle Bujard、Véronique Gouverneur、Charles Mioskowski

  DOI：10.1002/1099-0690(20021)2002:1<139::aid-ejoc139>3.0.co;2-s

  日期：2002.1

  The synthesis of the first two haptens designed to elicit catalytic hydrolytic antibodies for the dynamic kinetic resolution of racemic 4-substituted 4H-oxazolin-5-ones is reported. A cyclic phosphinate and a 2,5-dihydro-1H-pyrrolium derivative were chosen as “first generation” haptens. The cyclic phosphinate was designed to mimic the higher energy transition state along the reaction coordinate for

  前两个半抗原的合成旨在引发催化水解抗体，用于外消旋 4-取代 4H-恶唑啉-5-ones 的动态动力学分辨率。环状次膦酸盐和 2,5-二氢-1H-吡咯衍生物被选为“第一代”半抗原。环状次膦酸盐旨在模拟水解过程中沿反应坐标的较高能量过渡态，而选择第二半抗原的二氢-1H-吡咯基团来产生可能使用“诱饵和开关”机制的水解抗体。以闭环复分解反应为关键步骤，成功制备了这两种半抗原。
• Antibody-Catalyzed Rearrangement of a Peptide Bond: Mechanistic and Kinetic Investigations
  作者：Louis J. Liotta、Richard A. Gibbs、Scott D. Taylor、Patricia A. Benkovic、Stephen J. Benkovic

  DOI：10.1021/ja00122a001

  日期：1995.5

  Catalysis of the deamidation of asparagine residues may provide a powerful method for the deactivation of proteins. Catalytic antibodies (Gibbs et al. Science 1992, 258, 803) have been induced that catalyze the deamidation of a model dipeptide through an intermediate succinimide. Investigations of the mechanistic characteristics of two such antibodies, RG2-23C7 and RG2-2E4, revealed their ability to accelerate the hydrolysis of either the R- or S-enantiomers of the succinimide by factors of 10-500-fold to yield differing ratios of the aspartate and isoaspartate products. The mixed product ratios imply that two tetrahedral binding sites of unequal effectiveness were induced in response to the tetrahedral mimics (a phosphinate or secondary hydroxyl) within the hapten structure. The antibody RG2-2E4 also catalyzes the deamidation of either the D- or L-asparagine within the dipeptide through the intermediate cyclic imide, resulting in a multistep reaction sequence featuring a series of tetrahedral transition states. pH-rate profiles do not implicate functional groups within the antibodies' combining sites for either the deamidation or hydrolytic reactions. The strategy of bifunctional or higher order transition state mimics should provide a route to developing catalytic antibodies for reactions requiring multistep processing.
• A Highly Efficient and Practical Synthesis of Cyclic Phosphinates Using Ring-Closing Metathesis
  作者：M. Bujard、V. Gouverneur、C. Mioskowski

  DOI：10.1021/jo981795j

  日期：1999.3.1
• US4102949A
  申请人：——

  公开号：US4102949A

  公开（公告）日：1978-07-25