(5R,1'S)-5-[1-(benzyloxycarbonylamino)-2-methylpropyl]-3-methylenedihydro-2(3H)-furanone | 221286-65-3

• 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: (5R,1'S)-5-[1-(benzyloxycarbonylamino)-2-methylpropyl]-3-methylenedihydro-2(3H)-furanone
• 英文别名: benzyl N-[(1S)-2-methyl-1-[(2R)-4-methylidene-5-oxooxolan-2-yl]propyl]carbamate
• CAS: 221286-65-3
• 化学式: C₁₇H₂₁NO₄
• 分子量: 303.358
• InChiKey: WSUVFYXJJHXUFX-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (5R,1'S)-5-[1-(benzyloxycarbonylamino)-2-methylpropyl]-3-methylenedihydro-2(3H)-furanone 在 sodium tetrahydroborate 作用下， 以39%的产率得到((1S,2R)-2,5-Dihydroxy-1-isopropyl-4-methyl-pentyl)-carbamic acid benzyl ester
  参考文献：
  名称：

  The synthesis of ketomethylene pseudopeptide analogues of dipeptide aldehyde inhibitors of calpain

  摘要：

  The ketomethylene phenylalanal and alanal analogues of Cbz-Val-Phe-H and Cbz-Val-Ala-H have been prepared and the K-i values versus chicken gizzard smooth muscle calpain were determined. The ketomethylene isosteres were significantly less potent than the corresponding dipeptide aldehydes, and this loss in activity is attributed to the absence of a critical interaction between the P1-P2 amide bond and the peptide binding region of calpain. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(98)00704-5
• 作为产物：
  描述：

  (2'R,3'S)-methyl 2-[3-(benzyloxycarbonylamino)-2-hydroxy-4-methylpentyl]propenoate 在 ion-exchange resin Dowex H⁽¹⁺⁾ 作用下， 以 乙醇 为溶剂， 反应 72.0h， 以63%的产率得到(5R,1'S)-5-[1-(benzyloxycarbonylamino)-2-methylpropyl]-3-methylenedihydro-2(3H)-furanone
  参考文献：
  名称：

  使用铟介导的Barbier烯丙基加成法从α-氨基酸中取代氨基烷基的α-亚甲基-γ-丁内酯

  摘要：

  Z-保护的α氨基醛的铟-介导的反应1 - 6与2-（溴甲基）丙烯酸酯8 / 9在水性溶剂中进行了研究。可以通过螯合物控制的反应来解释偏爱形成顺式配置的烯丙基醇10 – 16（非对映选择性范围为2：1至32：1，收率68–93％）。在氨基醛的制备和转化过程中未发生外消旋作用。酸催化的酯化反应（在Et 2 O中为H 2 SO 4）导致α-亚甲基-γ-丁内酯17 – 22产率从89％到97％不等。通过五个X射线晶体学分析和NMR谱图的比较，确定了所有非对映异构体的构型。

  DOI：

  10.1002/(sici)1099-0690(199907)1999:7<1551::aid-ejoc1551>3.0.co;2-8

文献信息

• Synthesis of Highly Functionalized Amino Acid and Hydroxy Acid Derivatives from γ‐Aminoalkyl‐Substituted α‐Methylene‐γ‐butyrolactones
  作者：Steffen Steurer、Joachim Podlech

  DOI：10.1002/1099-0690(200203)2002:5<899::aid-ejoc899>3.0.co;2-#

  日期：2002.3

  reductive cleavage of the hydroxy and the benzyl groups under hydrogenolytic conditions afforded a diaminocarboxylic acid derivative. Addition of S-nucleophiles furnished the corresponding 1,4 adducts in excellent yields and with good selectivities, especially when a cysteine derivative was used as nucleophile. Hydrogenation of the α-methylene-γ-butyrolactones provided α-methyl-substituted lactones,

  将C-，S-，N-和O-亲核试剂加到α-氨基酸衍生的α-亚甲基-γ-丁内酯中可提供相应的迈克尔加合物。分别以优异的选择性可以实现添加铜酸盐或氰化物。丙二酸根阴离子或甲醇盐的添加可以以良好的产率进行，但是选择性很差。的加成Ñ -nucleophiles用实现Ñ-苄基羟胺。在氢解条件下羟基和苄基的进一步还原裂解得到二氨基羧酸衍生物。S-亲核试剂的添加以优异的产率和良好的选择性提供了相应的1,4加合物，特别是当半胱氨酸衍生物用作亲核试剂时。α-亚甲基-γ-丁内酯的氢化提供α-甲基取代的内酯，并且臭氧分解产生相应的α，β-二羰基化合物。用氯化铑作为催化剂，将外环双键异构化为内环双键。通过X射线晶体学分析和NMR光谱（包括NOE实验）确定了所有产品的构型。
• Aminoalkyl-Substituted α-Methylene-γ-butyrolactones from α-Amino Acids Using an Indium-Mediated Barbier Allyl Addition
  作者：Steffen Steurer、Joachim Podlech

  DOI：10.1002/(sici)1099-0690(199907)1999:7<1551::aid-ejoc1551>3.0.co;2-8

  日期：1999.7

  The indium-mediated reaction of Z-protected α-amino aldehydes 1–6 with 2-(bromomethyl)acrylates 8/9 in aqueous solvents has been investigated. The preference for the formation of syn-configured homoallyl alcohols 10–16 (diastereoselectivities ranging from 2:1 to 32:1, yields 68–93%) may be explained by a chelate-controlled reaction. No racemization occurred during the preparation and transformation

  Z-保护的α氨基醛的铟-介导的反应1 - 6与2-（溴甲基）丙烯酸酯8 / 9在水性溶剂中进行了研究。可以通过螯合物控制的反应来解释偏爱形成顺式配置的烯丙基醇10 – 16（非对映选择性范围为2：1至32：1，收率68–93％）。在氨基醛的制备和转化过程中未发生外消旋作用。酸催化的酯化反应（在Et 2 O中为H 2 SO 4）导致α-亚甲基-γ-丁内酯17 – 22产率从89％到97％不等。通过五个X射线晶体学分析和NMR谱图的比较，确定了所有非对映异构体的构型。
• The synthesis of ketomethylene pseudopeptide analogues of dipeptide aldehyde inhibitors of calpain
  作者：Michael R. Angelastro、Angela L. Marquart、Shujaath Mehdi、Jack R. Koehl、Roy J. Vaz、Philippe Bey、Norton P. Peet

  DOI：10.1016/s0960-894x(98)00704-5

  日期：1999.1

  The ketomethylene phenylalanal and alanal analogues of Cbz-Val-Phe-H and Cbz-Val-Ala-H have been prepared and the K-i values versus chicken gizzard smooth muscle calpain were determined. The ketomethylene isosteres were significantly less potent than the corresponding dipeptide aldehydes, and this loss in activity is attributed to the absence of a critical interaction between the P1-P2 amide bond and the peptide binding region of calpain. (C) 1999 Elsevier Science Ltd. All rights reserved.