(R)-2,2'-二羟基-[1,1'-联萘]-3,3'-二醛 | 121314-69-0

• 物质功能分类: 化学试剂 - 有机试剂 - 多环化合物
• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 中文名称: (R)-2,2'-二羟基-[1,1'-联萘]-3,3'-二醛
• 中文别名: (S)-2,2'-二羟基-1,1'-联萘-3,3'醛基；(R)-2,2’-二羟基-[1,1’-联萘]-3,3’-二甲醛；(R)-2,2-二羟基-[1,1-联萘]-3,3-二醛；(R)-2,2'-二羟基-[1,1'-联萘]-3,3'-二甲醛
• 英文名称: (Ra)-2,2'-dihydroxy-1,1'-binaphthalenyl-3,3'-dicarbaldehyde
• 英文别名: (R)-3,3'-diformyl-2,2'-dihydroxy-1,1'-binaphthyl；(R)-2,2'-dihydroxy-1,1'-binaphthyl-3,3'-dicarbaldehyde；(R)-3,3'-diformyl-1,1'-bi-2-naphthol；(R)-3,3'-diformylbinol；(R)-2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarbaldehyde；(R)-2,2′-dihydroxy-1,1′-binaphthyl-3,3′-dicarbaldehyde；2,2'-dihydroxy-[1,1'-binaphthalene]-3,3'-dicarbaldehyde；(R)-2,2'-Dihydroxy-[1,1'-binaphthalene]-3,3'-dicarboxaldehyde；4-(3-formyl-2-hydroxynaphthalen-1-yl)-3-hydroxynaphthalene-2-carbaldehyde
• CAS: 121314-69-0
• 化学式: C₂₂H₁₄O₄
• 分子量: 342.351
• InChiKey: DENRDANQMQOFEU-UHFFFAOYSA-N

物化性质

• 熔点：
  285 °C
• 沸点：
  499.8±45.0 °C(Predicted)
• 密度：
  1.407±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险性防范说明：
  P261,P280,P301+P312,P302+P352,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335
• 储存条件：
  | 室温 |

反应信息

• 作为反应物：
  描述：

  (R)-2,2'-二羟基-[1,1'-联萘]-3,3'-二醛 以 乙醇 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Tuning the CD Spectrum and Optical Rotation Value of a New Binaphthalene Molecule with Two Spiropyran Units:  Mimicking the Function of a Molecular “AND” Logic Gate and a New Chiral Molecular Switch

  摘要：

  With the view to developing new chiral molecular switches and logic gates, a new binaphthalene molecule with two spiropyran units (1) was synthesized and characterized. Absorption and H-1 NMR spectral studies of 1 after reaction with acid/base indicate acidichromism can occur to compound 1. The synergistic actions of acid and UV light irradiation result in a remarkable change for the CD spectrum of the relatively dilute solution of 1, mimicking the behavior of a chiral "AND" gate, since the "ouput" is the CD signal. Furthermore, the optical rotation value of the relatively concentrated solution of 1 can be reversibly tuned after sequential reactions with acid and base, and thus a chiral molecular switch with nondestructive "output" signal is realized. The present results not only add a new example of chiral molecular switch with nondestructive readout but also provide a chiral "AND" gate based on the axial chiral binaphthalene to which switchable units are linked.

  DOI：

  10.1021/jo050489k
• 作为产物：
  描述：

  (R)-(+)-2,2’-双(甲氧基甲氧基)-1,1’-联萘 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 水 为溶剂， 反应 9.0h， 生成 (R)-2,2'-二羟基-[1,1'-联萘]-3,3'-二醛
  参考文献：
  名称：

  BINOL-based chiral aggregation-induced emission luminogens and their application in detecting copper(ii) ions in aqueous media

  摘要：

  在这项工作中，报道了两种手性发光物质。它们表现出聚集诱导发光和CD性能的湮灭。同时，其中一种可以作为铜离子的手性荧光传感器。

  DOI：

  10.1039/c5tc02778k

文献信息

• Biaryl-Based Macrocyclic and Polymeric Chiral (Salophen)Ni(II) Complexes:  Synthesis and Spectroscopic Study
  作者：Hui-Chang Zhang、Wei-Sheng Huang、Lin Pu

  DOI：10.1021/jo001276s

  日期：2001.1.1

  Polymeric/oligomeric and macrocyclic (salophen)Ni(II) complexes have been synthesized starting from both an achiral biphenol dialdehyde and an optically active BINOL dialdehyde. It was found that these polysalophens contain nonplanar coordination of Ni(II) units that are paramagnetic. This is different from the previously reported (salophen)Ni(II) complexes which are square planar and diamagnetic. The

  已从非手性双酚二醛和光学活性的BINOL二醛开始合成了高分子/低聚和大环（salophen）Ni（II）配合物。已发现这些聚salophophens包含顺磁性Ni（II）单元的非平面配位。这不同于先前报道的方形平面且抗磁性的（盐酚）Ni（II）配合物。非平面（salophen）Ni（II）单元使新的聚合Ni（II）络合物不同于为包含方形平面（salophen）Ni（II）单元的手性联芳基聚合物建议的螺旋结构。手性联萘单体与非手性联苯单体的共聚表明联萘单元的手性不沿着联苯聚合物链传播。
• Chiral Macrocycle-Catalyzed Highly Enantioselective Phenylacetylene Addition to Aliphatic and Vinyl Aldehydes
  作者：Zi-Bo Li、Tian-Dong Liu、Lin Pu

  DOI：10.1021/jo070091j

  日期：2007.6.1

  The 1,1‘-binaphthyl macrocycle (S)-2 is found to be an excellent catalyst for the alkyne addition to aldehydes. In the presence of (S)-2 (20 mol %) and Me2Zn (2 equiv) in THF at room temperature, the addition of phenylacetylene to linear or branched aliphatic aldehydes and vinyl aldehydes gave various propargylic alcohols with 89−96% ee.

  发现1,1'-联萘大环（S）-2是炔烃加成醛的极佳催化剂。在室温下，在THF中存在（S）-2（20 mol％）和Me 2 Zn（2当量）的情况下，将苯乙炔添加到直链或支链脂族醛和乙烯基醛中，制得89-96％的各种炔丙醇ee。
• Chiral basket-handle porphyrin-Co complexes for the catalyzed asymmetric cycloaddition of CO 2 to epoxides
  作者：Xiying Fu、Xinyao Jing、Lili Jin、Lilong Zhang、Xiaofeng Zhang、Bin Hu、Huanwang Jing

  DOI：10.1016/s1872-2067(18)63023-2

  日期：2018.5

  which have different chirality, and then applied to the coupling of propylene oxide and CO2 for generating chiral cyclic carbonates with good enantioselectivity under extremely mild conditions in the presence of tetrabutyl ammonium chloride as a co-catalyst. The good enantioselectivity in the cycloaddition reaction is attributed to a synergistic interplay between the chiral porphyrin catalysts and the

  摘要 通过将 CO2 环加成到环氧化物催化合成环状碳酸酯是固定 CO2 的标准方法。为此，设计、制备了手性篮柄卟啉-钴配合物，并通过核磁共振、质谱、傅里叶变换红外光谱、紫外-可见光谱和比旋光度对其进行了充分表征。所提出的金属卟啉催化剂是用具有不同手性的 1,1'-双-2-萘酚或 L-苯丙氨酸合成的，然后应用于环氧丙烷和 CO2 的偶联，以在极其温和的条件下生成具有良好对映选择性的手性环状碳酸酯。在四丁基氯化铵作为助催化剂存在的条件下。环加成反应中良好的对映选择性归因于手性卟啉催化剂和底物之间的协同相互作用。讨论了不对称环加成反应的机理和对映选择性。
• Enantioselective addition of diethylzinc to aldehydes in the presence of chiral hydrazone and imine ligands
  作者：Takashi Mino、Atsushi Suzuki、Masakazu Yamashita、Shusaku Narita、Yoshiaki Shirae、Masami Sakamoto、Tsutomu Fujita

  DOI：10.1016/j.jorganchem.2006.07.006

  日期：2006.10

  Optically active hydrazone and imine were found to act as effective ligands for enantioselective addition of diethylzinc to aldehydes. This reaction provided optically active secondary alcohols with ee up to 71%.

  发现光学活性和亚胺可作为二乙基锌对醛对映选择性加成的有效配体。该反应提供了具有高达71％ee的旋光仲醇。
• Highly enantioselective fluorescent recognition of amino acid derivatives by unsymmetrical salan sensors
  作者：Xia Yang、Kang Shen、Xuechao Liu、Chengjian Zhu、Yixiang Cheng

  DOI：10.1016/j.tetlet.2011.06.084

  日期：2011.9

  unsymmetrical salan fluorescent sensors 2a and 2b have been designed and synthesized. The chiral recognition of N-Boc-protected amino acids by 2a and 2b has been investigated. Sensor 2a possesses higher sensitivity and enantioselectivity than sensor 2b does. Job analysis and nonlinear regression results show that 2a can form a 1:1 stoichiometric complex with a N-Boc-protected amino acid. The obtained response

  已经设计并合成了新颖的不对称的萨兰荧光传感器2a和2b。已经研究了2a和2b对N -Boc保护的氨基酸的手性识别。传感器2a比传感器2b具有更高的灵敏度和对映选择性。作业分析和非线性回归结果表明2a可以与N -Boc保护的氨基酸形成1：1的化学计量配合物。获得的响应选择性和缔合常数表明2a是对N的高度对映选择性和灵敏的荧光传感器-Boc保护的氨基酸。