(+/-)-2-hydroxycyclobutanone dimethyl acetal | 42082-99-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+/-)-2-hydroxycyclobutanone dimethyl acetal
• 英文别名: 1-hydroxy-2,2-dimethoxycyclobutane；2,2-Dimethoxy-cyclobutanol；2,2-Dimethoxycyclobutan-1-ol
• CAS: 42082-99-5
• 化学式: C₆H₁₂O₃
• 分子量: 132.159
• InChiKey: AGUUATVSVNTRQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  9
• 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：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (+/-)-2-hydroxycyclobutanone dimethyl acetal 在 Pseudomonas cepacia lipase immobilized on Hyflo Super Cell 作用下， 以 正己烷 为溶剂， 反应 144.0h， 以30%的产率得到2-羟基环丁酮
  参考文献：
  名称：

  The first synthesis of both enantiomers of 2-hydroxycyclobutanone acetals by enzymatic transesterification: preparation of (R)-(+)-2-benzyloxycyclobutanone and its antipode

  摘要：

  A new practical enzymatic synthesis of (R)-(+)- and (S)-(-)-2-acetoxycyclobutanone acetals with 97-99.9% ee has been carried out via enzymatic transesterification of readily available racemic 2-hydroxycyclobutanone acetals. The absolute configuration has been established by X-ray analysis of the corresponding (S)-naproxenyl derivative. The first preparation of enantiomerically pure (R)-(+)- and (S)- (-)-2- benzyloxycyclobutanones was accomplished by means of protection of the hydroxy group followed by deacetalation reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.016
• 作为产物：
  描述：

  甲醇 、 二(三甲基硅氧基)环丁烯 反应 2.0h， 以84%的产率得到(+/-)-2-hydroxycyclobutanone dimethyl acetal
  参考文献：
  名称：

  The first synthesis of both enantiomers of 2-hydroxycyclobutanone acetals by enzymatic transesterification: preparation of (R)-(+)-2-benzyloxycyclobutanone and its antipode

  摘要：

  A new practical enzymatic synthesis of (R)-(+)- and (S)-(-)-2-acetoxycyclobutanone acetals with 97-99.9% ee has been carried out via enzymatic transesterification of readily available racemic 2-hydroxycyclobutanone acetals. The absolute configuration has been established by X-ray analysis of the corresponding (S)-naproxenyl derivative. The first preparation of enantiomerically pure (R)-(+)- and (S)- (-)-2- benzyloxycyclobutanones was accomplished by means of protection of the hydroxy group followed by deacetalation reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.016

文献信息

• Carbocation-Forming Reactions in Ionic Liquids
  作者：Xavier Creary、Elizabeth D. Willis、Madeleine Gagnon

  DOI：10.1021/ja0536623

  日期：2005.12.1

  water in the ionic liquid. The triflate derivative of pivaloin, trans-2-phenylcyclopropylcarbinyl mesylate, 2,2-dimethoxycyclobutyl triflate, the mesylate derivative of diethyl (phenylhydroxymethyl)-thiophosphonate, and Z-1-phenyl-5-trimethylsilyl-3-penten-1-yl trifluoroacetate all give products derived carbocation rearrangements (kDelta processes). anti-7-Norbornenyl mesylate gives products with complete

  已经在离子液体中研究了许多三氟乙酸盐、甲磺酸盐和三氟甲磺酸盐。几条证据表明，所有这些底物都通过电离反应生成碳阳离子中间体。例如，三氟乙酸枯基酯主要产生消除产物，但 -3.74 的 Hammett rho+ 值与碳阳离子过程一致。类似的 exo-2-phenyl-endo-3-deutero-endo-bicyclo[2.2.1]hept-2-yl trifluoroacetate 消除了外氢从阳离子中间体丢失的情况。1-金刚烷基甲磺酸酯和 2-金刚烷基三氟甲磺酸酯反应生成简单的取代产物，该产物源自离子液体中残留水对 1- 和 2-金刚烷基碳正离子的捕获。新戊酸的三氟甲磺酸酯衍生物，反式-2-苯基环丙基甲磺酸酯，2,2-二甲氧基环丁基三氟甲磺酸酯，(苯基羟甲基)-硫代膦酸二乙酯的甲磺酸酯衍生物和 Z-1-苯基-5-三甲基甲硅烷基-3-戊烯-1-基三氟乙酸酯均产生衍生的碳正离子重排产物（kDelta
• Stereoselective synthesis of (1R,2R)-1-amino-2-hydroxycyclobutanecarboxylic acid—serine derivative—, from racemic or optically active 2-benzyloxycyclobutanone
  作者：Damien Hazelard、Antoine Fadel、Christian Girard

  DOI：10.1016/j.tetasy.2006.05.014

  日期：2006.5

  one-pot reaction from readily available 2-benzyloxycyclobutanone gave, by means of an asymmetric Strecker synthesis, a kinetic or thermodynamic nitrile with good selectivity. After separation, the major trans-amino nitrile underwent basic hydrolysis and hydrogenolysis, followed by acidic hydrolysis, to give optically active (1R,2R)-1-amino-2-hydroxycyclobutanecarboxylic acid, serine derivative. The absolute

  通过不对称的Strecker合成，由容易获得的2-苄氧基环丁酮进行的简单高效的一锅反应可生成具有良好选择性的动力学或热力学腈。分离后，将主要的反式-氨基腈进行碱性水解和氢解，然后进行酸性水解，得到旋光性的（1 R，2 R）-1-氨基-2-羟基环丁烷羧酸，丝氨酸衍生物。通过对相应的顺式-氨基腈的X射线分析已经确定了绝对构型。
• Imaging Agents
  申请人：Goodman M. Mark

  公开号：US20070082879A1

  公开（公告）日：2007-04-12

  The present invention provides novel amino acid compounds useful in detecting and evaluating brain and body tumors. These compounds have the advantageous properties of rapid uptake and prolonged retention in tumors and can be labeled with halogen isotopes such as fluorine-18, iodine-123, iodine-124, iodine-125, iodine-131, bromine-75, bromine-76, bromine-77, bromine-82, astatine-210, astatine-211, and other astatine isotopes. These compounds can also be labeled with technetium and rhenium isotopes using known chelation complexes. The compounds disclosed herein bind tumor tissues in vivo with high specificity and selectivity when administered to a subject. Preferred compounds show a target to non-target ratio of at least 2:1, are stable in vivo and substantially localized to target within 1 hour after administration. Preferred compounds include 1-amino-2-[ 18 F]fluorocyclobutyl-1-carboxylic acid (2-[ 18 F]FACBC) and 1-amino-2-[ 18 F]fluoromethylcyclobutyl-1-carboxylic acid (2-[ 18 F]FMACBC). The labeled amino acid compounds of the invention are useful as imaging agents in detecting and/or monitoring tumors in a subject by PET or SPECT.
• IMAGING AGENTS
  申请人：GOODMAN Mark M.

  公开号：US20110144483A1

  公开（公告）日：2011-06-16

  The present invention provides novel amino acid compounds useful in detecting and evaluating brain and body tumors. These compounds have the advantageous properties of rapid uptake and prolonged retention in tumors and can be labeled with halogen isotopes such as fluorine-18, iodine-123, iodine-124, iodine-125, iodine-131, bromine-75, bromine-76, bromine-77, bromine-82, astatine-210, astatine-211, and other astatine isotopes. These compounds can also be labeled with technetium and rhenium isotopes using known chelation complexes. The compounds disclosed herein bind tumor tissues in vivo with high specificity and selectivity when administered to a subject. Preferred compounds show a target to non-target ratio of at least 2:1, are stable in vivo and substantially localized to target within 1 hour after administration. Preferred compounds include 1-amino-2-[ 18 F]fluorocyclobutyl-1-carboxylic acid (2-[ 18 F]FACBC) and 1-amino-2-[ 18 F]fluoromethylcyclobutyl-1-carboxylic acid (2-[ 18 F]FMACBC). The labeled amino acid compounds of the invention are useful as imaging agents in detecting and/or monitoring tumors in a subject by PET or SPECT.
• US7837982B2
  申请人：——

  公开号：US7837982B2

  公开（公告）日：2010-11-23