α-Hydroxy-β-acetyl-γ-phenyl-Δ^α,β-butenolid | 21053-80-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: α-Hydroxy-β-acetyl-γ-phenyl-Δ^α,β-butenolid
• 英文别名: 2(5H)-Furanone, 4-acetyl-3-hydroxy-5-phenyl-；3-acetyl-4-hydroxy-2-phenyl-2H-furan-5-one
• CAS: 21053-80-5
• 化学式: C₁₂H₁₀O₄
• 分子量: 218.209
• InChiKey: NAONGLJFJCQBGM-UHFFFAOYSA-N

物化性质

• 熔点：
  169-170 °C(Solv: methanol (67-56-1))
• 沸点：
  457.9±45.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  α-Hydroxy-β-acetyl-γ-phenyl-Δ^α,β-butenolid 在 zinc diacetate 作用下， 以 乙二醇 为溶剂， 反应 5.0h， 以83%的产率得到苄叉丙酮
  参考文献：
  名称：

  Bonadies, Francesco; Scarpati, M. Luisa; Savagnone, Fulvio, Gazzetta Chimica Italiana, 1982, vol. 112, # 1/2, p. 1 - 4

  摘要：

  DOI：
• 作为产物：
  描述：

  苯甲醛 、 methyl acetylpyruvate sodium salt 以 甲醇 、 水 为溶剂， 反应 4.0h， 以77%的产率得到α-Hydroxy-β-acetyl-γ-phenyl-Δ^α,β-butenolid
  参考文献：
  名称：

  Bonadies, Francesco; Scarpati, M. Luisa; Savagnone, Fulvio, Gazzetta Chimica Italiana, 1982, vol. 112, # 1/2, p. 1 - 4

  摘要：

  DOI：

文献信息

• Physicochemical properties of isomeric azines of 3-acetyl-4-hydroxy-2-methoxy-4-phenylcrotonic acid lactones.
  作者：TAKUSHI KURIHARA、KEIKO NASU、MASATOSHI INOUE、TOSHIMASA ISHIDA

  DOI：10.1248/cpb.31.912

  日期：——

  X-Ray crystallographic analyses of two isomeric azines of 3-acetyl-4-(2-chlorophenyl)-4-hydroxy-2-methoxycrotonic acid lactones (5b and 6b), which were pepared by reaction of 1b with hydrazine dihydrochloride, were carried out. The stereochemical difference between 5b (red needles) and 6b (yellow needles) is mainly in the =N-N= bonding mode ; this group takes the completely planar conformation in 5b, and the twisted conformation in 6b. From the results of energy calculations, thermal analyses, and epimerization reactions, it could be concluded that the yellow crystals (6) are structurally more stable than the red crystals (5).

  我们对 1b 与肼二盐酸盐反应生成的 3-乙酰基-4-(2-氯苯基)-4-羟基-2-甲氧基巴豆酸内酯的两种异构氮化物（5b 和 6b）进行了 X 射线晶体学分析。5b （红色针状）和 6b（黄色针状）之间的立体化学差异主要体现在 =N-N= 键合模式上；在 5b 中，该基团呈完全平面构象，而在 6b 中则呈扭曲构象。从能量计算、热分析和外延反应的结果来看，黄色晶体（6）的结构比红色晶体（5）更稳定。
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• KURIHARA T.; SAKAMOTO Y.; KOBAYASHI T.; MORI M., J. HETEROCYCL. CHEM., 1978, 15, NO 5, 737-743
  作者：KURIHARA T.、 SAKAMOTO Y.、 KOBAYASHI T.、 MORI M.

  DOI：——

  日期：——