tert-butyl S-α-bromopropionate | 98104-35-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl S-α-bromopropionate
• 英文别名: (S)-tert-butyl 2-bromopropanoate；tert-butyl (S)-2-bromopropanoate；(S)-tert-butyl bromopropionate；(S)-(-)-2-bromo-propionic acid tert-butyl ester；tert.-butyl (S)-α-bromopropionate；tert-butyl (S)-α-bromopropionate；tert-butyl (2S)-2-bromopropanoate
• CAS: 98104-35-9
• 化学式: C₇H₁₃BrO₂
• 分子量: 209.083
• InChiKey: CVAWKJKISIPBOD-YFKPBYRVSA-N

物化性质

• 沸点：
  170.2±8.0 °C(Predicted)
• 密度：
  1.297±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  tert-butyl S-α-bromopropionate 在 钯 氢气 、 氢气 、 caesium carbonate 作用下， 反应 20.0h， 生成 (S)-2-Amino-propionic acid (R)-1-tert-butoxycarbonyl-ethyl ester
  参考文献：
  名称：

  Stereoselektive synthese von D-α-hydroxycarbonsäuren bzw. D-α-hydroxycarbonsäuren enthaltenden depsipeptiden aus L-aminosäuren

  摘要：

  DOI：

  10.1016/s0040-4039(00)95009-3
• 作为产物：
  描述：

  (S)-(-)-2-溴丙酸 、 异丁烯 在 氢气 作用下， 以75%的产率得到tert-butyl S-α-bromopropionate
  参考文献：
  名称：

  Stereoselektive synthese von D-α-hydroxycarbonsäuren bzw. D-α-hydroxycarbonsäuren enthaltenden depsipeptiden aus L-aminosäuren

  摘要：

  DOI：

  10.1016/s0040-4039(00)95009-3

文献信息

• Method for synthesizing oxazinones
  申请人：——

  公开号：US20030232820A1

  公开（公告）日：2003-12-18

  New methods and intermediates are discussed for the stereospecific synthesis of oxazinone compounds.

  讨论了用于氧杂环酮化合物立体特异合成的新方法和中间体。
• Cyclic hydroxamates, especially multiply substituted [1,2]oxazinan-3-ones
  作者：Saul Wolfe、Marie-Claire Wilson、Ming-Huei Cheng、Gennady V Shustov、Christiana I Akuche

  DOI：10.1139/v03-122

  日期：2003.8.1

  Routes to putative N-acyl-D-ala-D-ala surrogates, beginning with the conversion of 4-, 5-, and 6-membered lactones into 5-, 6-, and 7-membered cyclic hydroxamates, are reported. The key step of the synthesis is trimethylaluminium-promoted cyclization of an ω-aminooxyester. The 7-membered cyclic hydroxamate crystallizes in a chair conformation. Extension of the reaction sequence to homoserine or homoserine lactone leads to cyclocanaline and N-acylated cyclocanalines. The 4-phenylacetamido derivative of cyclocanaline crystallizes in a boat conformation. The attachment of a 2-carboxypropyl substituent to the ring nitrogen of a 4-acylaminocyclocanaline has been effected, prior to cyclization, by coupling of the acyclic aminooxyester precursor to the triflate of benzyl lactate or, after cyclization, by coupling to tert-butyl α-bromopropionate in the presence of potassium fluoride – alumina, followed by removal of the protecting group in each case. A six-membered homolog of the antibiotic lactivicin has been synthesized by the reaction of 4-phenylacetamidocyclocanaline with benzyl 2-oxoglutarate in the presence of carbodiimide, followed by hydrogenolysis. Starting with methyl 2,4-dibromo-2,4-dideoxy-L-erythronate, which is available in two steps from L-ascorbic acid, these reaction sequences have been applied to the stereospecific synthesis of a D-alanine derivative whose nitrogen atom is enclosed within a 3,4-disubstituted [1,2]oxazinan-3-one. Key words: D-ala-D-ala surrogate, cyclocanaline, homolactivicin, peptidoglycan, trimethylaluminium.

  报道了将假定的N-酰-D-阿拉-D-阿拉替代物的合成途径，从将4、5和6元环内酯转化为5、6和7元环氢氧化物开始。合成的关键步骤是ω-氨氧酯的三甲基铝促进的环化反应。7元环氢氧化物以椅式构象结晶。将反应序列扩展到同型丝氨酸或同型丝氨酸内酯会导致环康纳林和N-酰化环康纳林的形成。环康纳林的4-苯乙酰氨基衍生物以船式构象结晶。在环康纳林的4-酰氨基环康纳林的环氮上附加2-羧基丙基取代基，可以通过将无环氨氧酯前体与苄乳酸三甲酯的三氟甲磺酸酯偶联，或在环化之后，通过与三氟甲基丙酸叔丁酯在氟化钾-氧化铝存在下偶联，然后在每种情况下去除保护基来实现。通过4-苯乙酰氨基环康纳林与苄基2-氧戊二酸酯在异亚胺存在下反应，然后进行氢解，合成了抗生素拉维西汀的六元同系物。从甲基2,4-二溴-2,4-二去氧-L-赤葡萄糖酸甲酯开始，该物质可以从抗坏血酸中经过两步合成，这些反应序列已被应用于立体特异性合成一种D-丙氨酸衍生物，其氮原子被包含在一个3,4-二取代[1,2]噁唑烷-3-酮内。关键词：D-ala-D-ala替代物，环康纳林，同型拉维西汀，肽聚糖，三甲基铝。
• New Class of Bright and Highly Stable Chiral Cyclen Europium Complexes for Circularly Polarized Luminescence Applications
  作者：Lixiong Dai、Wai-Sum Lo、Ian D. Coates、Robert Pal、Ga-Lai Law

  DOI：10.1021/acs.inorgchem.6b01546

  日期：2016.9.6

  recorded in our series of newly designed macrocyclic europium(III) complexes. A sterically locking approach involving a bidentate chromophore is adopted to control the formation of one stereoisomer, giving rise to extreme rigidity, high stability, and high emission intensity. The combination of a chiral substituent on a macrocyclic chelate for lanthanide ions opens up new perspectives for the further

  高克LUM 0.30（Δ的值Ĵ = 1，591纳米，在DMSO中）和-0.23（Δ Ĵ = 1，589纳米，H中2 O）被记录在我们的系列新设计的大环铕（III）络合物的。采用包括二齿生色团的空间锁定方法来控制一种立体异构体的形成，从而产生极高的刚性，高稳定性和高发射强度。镧系离子在大环螯合物上的手性取代基的结合为光学和生物应用中的圆偏振发光手性标签的进一步发展开辟了新的前景。
• Stereoselective syntheses of substituted succinic acid derivatives of the iron chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)]
  作者：George Bashiardes、Graham J. Bodwell、Stephen P. Collingwood、James F. Costello、Stephen G. Davies、Ai M. Fletcher、Alan Garner、Simon C. Preston、James E. Thomson

  DOI：10.1016/j.tet.2014.09.049

  日期：2014.11

  A range of alkyl- or aryl-substituted iron succinoyl complexes, incorporating the iron chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)], were prepared in high regio- and diastereoselectivities by employing four successful strategies: (i) the alkylation of chiral enolate equivalents with tert-butyl bromoacetate; (ii) the mutual kinetic resolution of tert-butyl α-bromoacetate with a chiral acetate enolate equivalent;

  一系列烷基-或芳基取代的琥珀铁配合物，结合有铁手性辅助剂[（η 5 -C 5 H ^ 5）的Fe（CO）（PPH 3）]中，在高区域选择性和非对映选择性通过采用四次成功制备策略：（i）用溴乙酸叔丁酯将手性烯醇盐当量烷基化；（ⅱ）的相互动力学拆分叔具有手性乙酸烯醇酯等效物的α-溴乙酸丁酯；（iii）手性琥珀酰烯醇酸酯等效物的烷基化；（iv）将有机锂试剂或酰胺化锂试剂共轭加到手性富马酰基衍生物上。表现出发生了铁手性助剂的氧化裂解，而没有损害琥珀酰片段的立体化学完整性。
• Substituted tetrahydroisoquinolines as C5a receptor modulators
  申请人：——

  公开号：US20040006069A1

  公开（公告）日：2004-01-08

  1 Substituted tetrahydroisoquinolines and related compounds are provided. Such compounds are ligands that may be used to modulate C5a receptor activity in vivo or in vitro, and are particularly useful in the treatment of conditions associated with pathological C5a receptor activation in humans, domesticated companion animals and livestock animals. Pharmaceutical compositions and methods for using them to treat such disorders are provided, as are methods for using such ligands for receptor localization studies.

  提供了替代四氢异喹啉和相关化合物。这些化合物是配体，可用于调节体内或体外的C5a受体活性，并且在治疗与人类、驯化伴侣动物和家畜动物中的病理性C5a受体激活相关的疾病方面特别有用。提供了用于治疗此类疾病的药物组成物和使用它们的方法，以及用于受体定位研究的配体使用方法。