(1R,2R,3S,4S)-3,4-Diphenyl-cyclobutane-1,2-dicarboxylic acid | 490-16-4

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 环丁烷木脂素
• 英文名称: (1R,2R,3S,4S)-3,4-Diphenyl-cyclobutane-1,2-dicarboxylic acid
• 英文别名: DL-(1R,2R,3S,4S)-3,4-diphenylcyclobutane-1,2-dicarboxylic acid；3c,4t-diphenyl-cyclobutane-1r,2t-dicarboxylic acid；3c,4t-Diphenyl-cyclobutan-1r,2t-dicarbonsaeure；(+/-)-δ-Truxinsaeure；opt.-inakt. 3^c.4^t-Diphenyl-cyclobutan-dicarbonsaeure-(1^c.2^t)；dl-δ-Truxinsaeure；(1R,2R,3S,4S)-3,4-diphenylcyclobutane-1,2-dicarboxylic acid
• CAS: 490-16-4；528-32-5；528-33-6；528-34-7；528-35-8；528-36-9；4482-52-4
• 化学式: C₁₈H₁₆O₄
• 分子量: 296.323
• InChiKey: QVNDSQQNODQYJM-CAOSSQGBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,4S)-3,4-Diphenyl-cyclobutane-1,2-dicarboxylic acid 在 氢氧化钾 、 氯化亚砜 、 乙醚 作用下， 生成 3,4-diphenyl-2-phenylcarbamoyl-cyclobutanecarboxylic acid
  参考文献：
  名称：

  Stoermer; Bacher, Chemische Berichte, 1922, vol. 55, p. 1879

  摘要：

  DOI：
• 作为产物：
  描述：

  β-truxinic acid 在 盐酸 作用下， 生成 (1R,2R,3S,4S)-3,4-Diphenyl-cyclobutane-1,2-dicarboxylic acid
  参考文献：
  名称：

  Stoermer; Scholtz, Chemische Berichte, 1921, vol. 54, p. 92

  摘要：

  DOI：

文献信息

• Photochemical reactions of trans-anethole
  作者：H. Nozaki、I. Otani、R. Noyori、M. Kawanisi

  DOI：10.1016/0040-4020(68)88120-7

  日期：1968.1

  obtained photochemically. The dimerization proceeds with strict stereospecificity and the structure of the dimer has been ascertained as 1,cis-2-di-p-anisyl-trans-3,trans-4-dimethylcyclobutane. The dimer was transformed into the corresponding diphenol, diacetate and 1,cis-2-dimethyl-trans-3,trans-4-diphenylcyclobutane. The hydrocarbon was independently obtained from β-truxinic acid by reduction. Some

  已经通过化学方法获得了新型的反式茴香脑二聚体。二聚化以严格的立体特异性进行，并且已经确定二聚体的结构为1，顺式-2-二-对-茴香基-反式-3，反式-4-二甲基环丁烷。将二聚体转化成相应的二酚，二乙酸酯和1，顺式-2-二甲基-反式-3，反式-4-二苯基环丁烷。烃是通过还原从β-精氨酸独立获得的。由肉桂酸二聚体类似地制备了一些二甲基二苯基环丁烷异构体，并比较了NMR光谱。
• Donor–acceptor fluorophores as efficient energy transfer photocatalysts for [2 + 2] photodimerization
  作者：Qing-An Wu、Feng Chen、Chen-Chao Ren、Xue-Fen Liu、Hao Chen、Liang-Xuan Xu、Xiao-Cong Yu、Shu-Ping Luo

  DOI：10.1039/c9ob02735a

  日期：——

  Mild [2 + 2] photodimerization of enone substrates was induced by donor-acceptor fluorophores. Enone substrates were activated efficiently for anti-head to head dimerizations with a high yield (up to 83%) and high selectivity. The adjustable excited state potential also allows donor-acceptor fluorophores to be used for isomerization of the above substrates, confirming the potential of donor-acceptor

  供体-受体荧光团诱导了烯酮底物的轻度[2 + 2]光二聚化。高效率（高达83％）和高选择性的Enone底物被有效激活，以防止头对头二聚化。可调的激发态电势还允许将供体-受体荧光团用于上述底物的异构化，证实了供体-受体荧光团作为能量转移光催化剂的潜力。
• Regioselective photodimerization of cinnamic acid in a micellar solution
  作者：Yushin Nakamura

  DOI：10.1039/c39880000477

  日期：——

  Irradiation of trans-cinnamic acid (1) and its methyl ester (2) in 1% aq. cetyltirmethylammonium bromide gave dimeric products in 35 and 29% yields as a mixture of truxinic and truuxillic acids in a ratio of 19 : 1 and 3.8 : 1, respectively, while in homogeneous solutions (1) gave no photodimers and (2) gave dimeric products in 2.3% yield under similar reaction conditions.

  在1％水溶液中辐照反肉桂酸（1）及其甲酯（2）。十六烷基甲基溴化铵以分别为19：1和3.8：1的比例的丁二酸和丁三酸的混合物形式分别提供35％和29％的收率的二聚产物，而在均相溶液中（1）不提供光二聚体，（2）产生二聚体产物在相似的反应条件下产率为2.3％。
• Control of solid-state photodimerization of trans-cinnamic acid by double salt formation with diamines
  作者：Yoshikatsu Ito、Bozena Borecka、James Trotter、John R Scheffer

  DOI：10.1016/0040-4039(95)01209-z

  日期：1995.8

  By double salt formation, diamines can steer the solid-state [2+2] photodimerization of trans-cinnamic acid (1). Thus, the yields for the photodimerization were significant only in three double salts, i.e., the ones with tn and t- and c-chxn, which are assumed to have an overlap structure. The resultant photodimer is generally β-truxinic acid, although in one case, ε-truxillic acid was formed. α-Truxillic

  通过形成双盐，二胺可以控制反式肉桂酸（1）的固态[2 + 2]光二聚化。因此，光二聚化的产率仅在三种复盐中才有意义，即具有tn和t-和c- chxn的那些，它们被认为具有重叠结构。所得的光二聚体通常是β-尿酸，尽管在一种情况下形成了ε-尿酸。所研究的任何一种复盐均未产生α-氨甲磺酸。三种低光反应性的双盐（1·en，1·pen，1·hen）的X射线晶体结构与施密特定律一致。
• Stereoselectivity control of [2 + 2] photocycloaddition by changing site distances of hydrotalcite interlayers
  作者：Tetsuya Shichi、Katsuhiko Takagi、Yasuhiko Sawaki

  DOI：10.1039/cc9960002027

  日期：——

  Stereoselectivity of photocyclodimers of unsaturated carboxylates is shown to be controlled by changing the site distance of clay interlayers.

  研究表明，不饱和羧酸盐光环二聚体的立体选择性可通过改变粘土夹层的位点距离来控制。