3-(4-methoxyphenyl)hydrocoumarin | 27247-02-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 3-(4-methoxyphenyl)hydrocoumarin
• 英文别名: 3-(4-methoxyphenyl)chroman-2-one；3-(4-Methoxyphenyl)-3,4-dihydrochromen-2-one
• CAS: 27247-02-5
• 化学式: C₁₆H₁₄O₃
• 分子量: 254.285
• InChiKey: OISBMAZFQAMJNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 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：

  3-(4-methoxyphenyl)hydrocoumarin 在 (S)-(+)-3,3′-双(3,5-双(三氟甲基)苯基)-1,1′-联萘-2,2′-二基磷酸氢酯 、 三甲基铝 作用下， 以 正己烷 、 二氯甲烷 、 环己烷 为溶剂， 反应 24.0h， 生成 (S)-3-(4-methoxyphenyl)spiro[chroman-2,2'-[1,3]dithiane]
  参考文献：
  名称：

  通过乙烯酮二硫缩醛的催化不对称质子化使 α-芳基氢化香豆素脱消旋

  摘要：

  描述了乙烯酮二硫缩醛的前所未有的催化不对称质子化。在手性布朗斯台德酸催化剂的存在下，各种外消旋 α-芳基氢化香豆素衍生物转化为对映体富集的二硫代缩醛保护的氢化香豆素。引入了一种新开发的磷酸，具有 3,5-双 (五氟硫代) 苯基 (3,5-(SF(5))(2)C(6)H(3)) 取代基。所得产物可以分别通过简单的水解或氢化容易地转化为氢化香豆素或相应的色满。

  DOI：

  10.1021/ja3096202
• 作为产物：
  描述：

  4-甲氧基苯乙酰氯 在 10% Pd/C 、 氢气 、 四丁基硫酸氢铵 、 potassium carbonate 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 生成 3-(4-methoxyphenyl)hydrocoumarin
  参考文献：
  名称：

  通过乙烯酮二硫缩醛的催化不对称质子化使 α-芳基氢化香豆素脱消旋

  摘要：

  描述了乙烯酮二硫缩醛的前所未有的催化不对称质子化。在手性布朗斯台德酸催化剂的存在下，各种外消旋 α-芳基氢化香豆素衍生物转化为对映体富集的二硫代缩醛保护的氢化香豆素。引入了一种新开发的磷酸，具有 3,5-双 (五氟硫代) 苯基 (3,5-(SF(5))(2)C(6)H(3)) 取代基。所得产物可以分别通过简单的水解或氢化容易地转化为氢化香豆素或相应的色满。

  DOI：

  10.1021/ja3096202

文献信息

• Pd-Catalyzed Decarboxylative Asymmetric Protonation of Sterically Hindered α-Aryl Lactones and Dihydrocoumarins
  作者：Jinju James、Ramulu Akula、Patrick J. Guiry

  DOI：10.1002/adsc.201800724

  日期：2018.8.17

  Pd‐catalyzed decarboxylative asymmetric protonation (DAP) has been developed for sterically hindered α‐aryl lactone and dihydrocoumarin substrates. Optimization studies were conducted using δ‐lactone‐ and dihydrocoumarin‐derived α‐aryl, β‐oxo‐allyl esters with 2,4,6‐trimethoxyphenyl as the aryl substituent. In the absence of a chiral P,N‐ligand, (1R,2S)‐(−)ephedrine, a cheap and readily available chiral

  钯催化的脱羧不对称质子化（DAP）已开发用于空间受阻的α-芳基内酯和二氢香豆素底物。使用由δ-内酯和二氢香豆素衍生的α-芳基，β-氧代烯丙基酯与2,4,6-三甲氧基苯基作为芳基取代基进行了优化研究。在没有手性P，N-配体的情况下，（1 R，2 S）-（-）麻黄碱（廉价且容易获得的手性质子供体）与内酯和二氢香豆素的对映选择性高达92％ee和88％ee基板。含双邻位的庞大芳基取代基和萘基的对映选择性最高，分别高达92％和86％。提出了立体化学原理来解释不对称诱导的优选含义。
• Polynucleotide encoding 2-hydorxyisoflavanone dehydratase and application of the same
  申请人：Ayabe Shinichi

  公开号：US20070050865A1

  公开（公告）日：2007-03-01

  2-Hydroxyisoflavanone dehydratase substantially having the amino acid sequence represented by SEQ ID NO: 1 is isolated from licorice. Further, a polynucleotide encoding 2-hydroxyisoflavanone dehydratase of the SEQ ID NO: 2 is obtained. Furthermore, the amino acid sequence of 2-hydroxyisoflavanone dehydratase is identified from soybean and a polynucleotide encoding 2-hydroxyisoflavanone dehydratase is obtained.

  2-羟基异黄酮酮脱水酶，其氨基酸序列主要由SEQ ID NO: 1表示，从甘草中分离出来。此外，获得了编码SEQ ID NO: 2的2-羟基异黄酮酮脱水酶的多核苷酸。此外，从大豆中鉴定出2-羟基异黄酮酮脱水酶的氨基酸序列，并获得了编码2-羟基异黄酮酮脱水酶的多核苷酸。
• Novel aromatic prenyltransferases, nucleic acids encoding same and uses therefor
  申请人：Kuzuyama Tomohisa

  公开号：US20060183211A1

  公开（公告）日：2006-08-17

  In accordance with the present invention, a novel aromatic prenyltransferase, Orf2 from Streptomyces sp. strain CL190, involved in naphterpin biosynthesis has been identified and the structure thereof elucidated. This prenyltransferase catalyzes the formation of a C—C bond between a prenyl group and a compound containing an aromatic nucleus, and also displays C—O bond formation activity. Numerous crystallographic structures of the prenyltransferase have been solved and refined, e.g., (1) prenyltransferase complexed with a buffer molecule (TAPS), (2) prenyltransferase as a binary complex with geranyl diphosphate (GPP) and Mg 2+ , and prenyltransferase as ternary complexes with a non-hydrolyzable substrate analogue, geranyl S-thiolodiphosphate (GSPP) and either (3) 1,6-dihydroxynaphthalene (1,6-DHN), or (4) flaviolin (i.e., 2,5,7-trihydroxy-1,4-naphthoquinone, which is the oxidized product of 1,3,6,8-tetrahydroxynaphthalene (THN)). These structures have been solved and refined to 1.5 Å, 2.25 Å, 1.95 Å and 2.02 Å, respectively. This first structure of an aromatic prenyltransferase displays an unexpected and non-canonical (β/α)-barrel architecture. The complexes with both aromatic substrates and prenyl containing substrates and analogs delineate the active site and are consistent with a proposed electrophilic mechanism of prenyl group transfer. These structures also provide a mechanistic basis for understanding prenyl chain length determination and aromatic co-substrate recognition in this structurally unique family of aromatic prenyltransferases. This structural information is useful for predicting the aromatic prenyltransferase activity of proteins.

  根据本发明，一种新型芳香族前基转移酶 Orf2 来自于 链霉菌 菌株 CL190 中发现的一种参与萘素生物合成的新型芳香族前基转移酶 Orf2，并阐明了其结构。这种炔基转移酶催化炔基与含有芳香核的化合物之间形成 C-C 键，同时还具有形成 C-O 键的活性。前炔基转移酶的许多晶体结构已得到解决和完善，例如：（1）前炔基转移酶与缓冲分子（TAPS）的复合物；（2）前炔基转移酶与二磷酸香叶酯（GPP）和 Mg 2+ 和 (3) 1,6-二羟基萘（1,6-DHN）或 (4) 黄素（即 2,5,7-三羟基-1,4-萘醌，它是 1,3,6,8-四羟基萘（THN）的氧化产物）的三元复合物。这些结构已分别求解并精炼至 1.5 Å、2.25 Å、1.95 Å 和 2.02 Å。这是首个芳香族预烯基转移酶的结构，显示出一种意想不到的非经典（β/α）桶状结构。与芳香底物和含预烯醇底物及类似物的复合物划定了活性位点，并与所提出的预烯醇基团转移的亲电机制相一致。这些结构还为了解这一结构独特的芳香族前酰基转移酶家族的前酰基链长决定和芳香族共底物识别提供了机理基础。这些结构信息有助于预测蛋白质的芳香族前基转移酶活性。
• NOVEL AROMATIC PRENYLTRANSFERASES, NUCLEIC ACIDS ENCODING SAME AND USES THEREFOR
  申请人：Kuzuyama Tomohisa

  公开号：US20080274478A1

  公开（公告）日：2008-11-06

  In accordance with the present invention, a novel aromatic prenyltransferase, Orf2 from Streptomyces sp. strain CL190, involved in naphterpin biosynthesis has been identified and the structure thereof elucidated. This prenyltransferase catalyzes the formation of a C—C bond between a prenyl group and a compound containing an aromatic nucleus, and also displays C—O bond formation activity. Numerous crystallographic structures of the prenyltransferase have been solved and refined, e.g., (1) prenyltransferase complexed with a buffer molecule (TAPS), (2) prenyltransferase as a binary complex with geranyl diphosphate (GPP) and Mg 2+ , and prenyltransferase as ternary complexes with a non-hydrolyzable substrate analogue, geranyl S-thiolodiphosphate (GSPP) and either (3) 1,6-dihydroxynaphthalene (1,6-DHN), or (4) flaviolin (i.e., 2,5,7-trihydroxy-1,4-naphthoquinone, which is the oxidized product of 1,3,6,8-tetrahydroxynaphthalene (THN)). These structures have been solved and refined to 1.5 Å, 2.25 Å, 1.95 Å and 2.02 Å, respectively. This first structure of an aromatic prenyltransferase displays an unexpected and non-canonical (β/α)-barrel architecture. The complexes with both aromatic substrates and prenyl containing substrates and analogs delineate the active site and are consistent with a proposed electrophilic mechanism of prenyl group transfer. These structures also provide a mechanistic basis for understanding prenyl chain length determination and aromatic co-substrate recognition in this structurally unique family of aromatic prenyltransferases. This structural information is useful for predicting the aromatic prenyltransferase activity of proteins.
• PLANT ISOFLAVONE AND ISOFLAVANONE O-METHYLTRANSFERASE GENES
  申请人：Broeckling Bettina E.

  公开号：US20080317880A1

  公开（公告）日：2008-12-25

  The invention provides enzymes that encode O-methyltransferases (OMTs) from Medicago truncatula that allow modification to plant (iso)flavonoid biosynthetic pathways. In certain aspects of the invention, the genes encoding these enzymes are provided. The invention therefore allows the modification of plants for isoflavonoid content. Transgenic plants comprising such enzymes are also provided, as well as methods for improving disease resistance in plants. Methods for producing food and nutraceuticals, and the resulting compositions, are also provided.