ethyl(2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenyl-2-hexenoate | 126399-04-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: ethyl(2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenyl-2-hexenoate
• 英文别名: (2E,4S,5S)-ethyl 5-methoxy-2,4-dimethyl-6-phenylhex-2-enoate；ethyl (E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenylhex-2-enoate
• CAS: 126399-04-0
• 化学式: C₁₇H₂₄O₃
• 分子量: 276.376
• InChiKey: NAJMRCFESOIERI-LDHVUCNQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl(2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenyl-2-hexenoate 在 manganese(IV) oxide 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 54.5h， 生成 (2E,4E,6S,7S)-7-methoxy-4,6-dimethyl-8-phenyl-2,4-octadienal
  参考文献：
  名称：

  Enantiospecific Synthesis of N-Boc-Adda:  A Linear Approach

  摘要：

  Synthesis of the unusual amino acid (2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6 decadienoic acid (Adda), a unit of numerous cyanobacterial toxins, is described. Construction of the target molecule was achieved in 13 steps with an overall yield of 40%. The work is highlighted by a novel one-pot transformation from isoxazolidin-5-one intermediate 6 to the final product, a step that can also be used to form beta-amino acids.

  DOI：

  10.1021/ol006347o
• 作为产物：
  描述：

  (2R,3S)-3-methoxy-2-methyl-4-phenylbutan-(N-methyl-O-methyl)-hydroxamide 在 二异丁基氢化铝 作用下， 生成 ethyl(2E,4S,5S)-5-methoxy-2,4-dimethyl-6-phenyl-2-hexenoate
  参考文献：
  名称：

  Enantiospecific Synthesis of N-Boc-Adda:  A Linear Approach

  摘要：

  Synthesis of the unusual amino acid (2S,3S,8S,9S)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyl-4,6 decadienoic acid (Adda), a unit of numerous cyanobacterial toxins, is described. Construction of the target molecule was achieved in 13 steps with an overall yield of 40%. The work is highlighted by a novel one-pot transformation from isoxazolidin-5-one intermediate 6 to the final product, a step that can also be used to form beta-amino acids.

  DOI：

  10.1021/ol006347o

文献信息

• Facile and rapid access to linear and truncated microcystin analogues for the implementation of immunoassays
  作者：G. Clavé、C. Ronco、H. Boutal、N. Kreich、H. Volland、X. Franck、A. Romieu、P.-Y. Renard

  DOI：10.1039/b920193a

  日期：——

  microcystin-LR analogues based on Adda [(2S,3S,8S,9S,4E,6E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldecadienoic acid] or its corresponding aldol precursor linked to a polypeptide moiety have been synthesised and assessed for their binding affinity by the monoclonal antibody mAb MC159, an anti-microcystin-LR mAb recently selected by us for the detection of microcystins through various immunoassay formats

  一系列简化 微囊藻毒素 基于Adda的类似物[（2 S，3 S，8 S，9 S，4 E，6 E）-3-氨基-9-甲氧基-2,6,8-三甲基-10-苯基癸二烯酸]或其连接至多肽部分的相应的羟醛前体已被合成并通过单克隆抗体评估其结合亲和力 单抗 MC159，抗微囊藻毒素-LR 单抗我们最近选择了通过各种免疫测定形式检测微囊藻毒素的方法。由Pearson等人开发的对N -Boc-Adda的对映体特异性合成已进行了一些修饰。（有机化学快报。，2000，2，2901）这使我们能够访问以经济和省时的方式MC-LR的线性类似物小型图书馆。作为示例，选择了Adda来合成由此衍生的荧光探针β-氨基酸。随后通过肟连接将该探针固相固定，以产生适于通过SPIT-FRI方法检测微囊藻毒素的生物芯片。
• Total Synthesis of Motuporin (Nodularin-V)
  作者：Shawn M. Bauer、Robert W. Armstrong

  DOI：10.1021/ja9811243

  日期：1999.7.1

  serine/threonine phosphatase (protein phosphatase 1 and 2A) inhibitors constitute a biologically and structurally interesting class of natural products. Among this class of inhibitors are cyclic pentapeptides (nodularins) and cyclic heptapeptides (microcystins), both of which inhibit at the nanomolar level and are the only peptide inhibitors of these enzymes. Described herein is the total synthesis of motuporin

  丝氨酸/苏氨酸磷酸酶（蛋白磷酸酶 1 和 2A）抑制剂构成了一类具有生物学和结构意义的天然产物。这类抑制剂包括环状五肽（nodularins）和环状七肽（微囊藻毒素），两者都在纳摩尔水平上进行抑制，并且是这些酶的唯一肽抑制剂。本文描述了 motuporin 的全合成，它利用 Ugi 四组分缩合 (4CC) 反应合成 2-(N)-甲基氨基丁烯基残基，Matteson 的用于构建关键片段的二卤甲基锂插入方法，以及整体合成策略适合合成类似物。
• Towards an asymmetric synthesis of ADDA conjugates
  作者：Darren J. Cundy、Andrew C. Donohue、Tom D. McCarthy

  DOI：10.1016/s0040-4039(98)00946-0

  日期：1998.7

  In order to develop a general synthesis of ADDA containing peptides, an asymmetric synthesis of the beta-lactam 4 and initial investigations into its opening with aminoesters is described. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Total synthesis of N-phthaloyl adda methyl ester: All stereocenters originating from a single chiral epoxyalcohol
  作者：T.K Chakraborty、S.P Joshi

  DOI：10.1016/s0040-4039(00)88911-x

  日期：1990.1
• Cundy, Darren J.; Donohue, Andrew C.; McCarthy, Tom D., Journal of the Chemical Society. Perkin transactions I, 1999, # 5, p. 559 - 567
  作者：Cundy, Darren J.、Donohue, Andrew C.、McCarthy, Tom D.

  DOI：——

  日期：——